FR2319373A1 - (2,2)-Diesterified diholosides prodn. - from cpd. with all other hydroxy gps. silylated, and a fatty acid or its reactive deriv. - Google Patents

(2,2)-Diesterified diholosides prodn. - from cpd. with all other hydroxy gps. silylated, and a fatty acid or its reactive deriv.

Info

Publication number
FR2319373A1
FR2319373A1 FR7523578A FR7523578A FR2319373A1 FR 2319373 A1 FR2319373 A1 FR 2319373A1 FR 7523578 A FR7523578 A FR 7523578A FR 7523578 A FR7523578 A FR 7523578A FR 2319373 A1 FR2319373 A1 FR 2319373A1
Authority
FR
France
Prior art keywords
silylated
fatty acid
diholosides
diesterified
prodn
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
FR7523578A
Other languages
French (fr)
Other versions
FR2319373B1 (en
Inventor
Raoul Toubiana
Marie-Josephe Carrieu Toubiana
Bhupesch Das
Edgar Lederer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bpifrance Financement SA
Original Assignee
Agence National de Valorisation de la Recherche ANVAR
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Agence National de Valorisation de la Recherche ANVAR filed Critical Agence National de Valorisation de la Recherche ANVAR
Priority to FR7523578A priority Critical patent/FR2319373A1/en
Priority to BE1007514A priority patent/BE844272A/en
Priority to DE19762633690 priority patent/DE2633690A1/en
Publication of FR2319373A1 publication Critical patent/FR2319373A1/en
Application granted granted Critical
Publication of FR2319373B1 publication Critical patent/FR2319373B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12

Abstract

Process for selective esterification of primary OH gps. in dihalosides (I) comprises reacting the acid halide or alkali metal of an opt. substd. fatty acid with (I) in which the 6-sec. OH's are silylated but the 2 primary OH's are free or replaced by a reactive gp. such as halo. The silylated OH's are deprotected after esterification and the product purified e.g. by chromatography. The diesters of (I) formed have adjuvant and immunotherapeutic activity, and are prepd. much purer than previously possible. The process gives excellent yields and is suitable for large-scale operation. An esp. pref. prod. is 6,6'-dipalmitoyl-alpha-D-trehalose. It was prepd. from trehalose by reaction with hexamethyl-disilazane; K2CO3-hydrolysis to remove only the 6,6'-trimethylsilyls; reaction with palmitoyl chloride; then deprotection with aq. methanol.
FR7523578A 1975-07-29 1975-07-29 (2,2)-Diesterified diholosides prodn. - from cpd. with all other hydroxy gps. silylated, and a fatty acid or its reactive deriv. Granted FR2319373A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
FR7523578A FR2319373A1 (en) 1975-07-29 1975-07-29 (2,2)-Diesterified diholosides prodn. - from cpd. with all other hydroxy gps. silylated, and a fatty acid or its reactive deriv.
BE1007514A BE844272A (en) 1975-07-29 1976-07-19 NEW PROCESS FOR SELECTIVE ESTERIFICATION OF PRIMARY ALCOHOL FUNCTIONS OF DIHOLOSIDES AND PRODUCTS THUS KEPT
DE19762633690 DE2633690A1 (en) 1975-07-29 1976-07-27 PROCESS FOR THE SELECTIVE ESTERIFICATION OF THE PRIMARY ALCOHOL FUNCTIONS OF DIHOLOSIDES CONTAINED WITH THE PRODUCTS AND THEIR THERAPEUTIC USE

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7523578A FR2319373A1 (en) 1975-07-29 1975-07-29 (2,2)-Diesterified diholosides prodn. - from cpd. with all other hydroxy gps. silylated, and a fatty acid or its reactive deriv.

Publications (2)

Publication Number Publication Date
FR2319373A1 true FR2319373A1 (en) 1977-02-25
FR2319373B1 FR2319373B1 (en) 1978-12-01

Family

ID=9158463

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7523578A Granted FR2319373A1 (en) 1975-07-29 1975-07-29 (2,2)-Diesterified diholosides prodn. - from cpd. with all other hydroxy gps. silylated, and a fatty acid or its reactive deriv.

Country Status (3)

Country Link
BE (1) BE844272A (en)
DE (1) DE2633690A1 (en)
FR (1) FR2319373A1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2355506A1 (en) * 1976-06-25 1978-01-20 Azuma Ichiro IMMUNOTHERAPY ADJUVANT CONTAINING GLYCOLIPID AS ACTIVE INGREDIENT AND PROCESS FOR PREPARATION
EP0005682A1 (en) * 1978-05-18 1979-11-28 Ciba-Geigy Ag Silyl-glucosamine derivatives, process for their preparation and medicines containing them
FR2477551A1 (en) * 1980-03-10 1981-09-11 Anvar NEW DERIVATIVES OF A-TREHALOSE AND MEDICAMENTS CONTAINING SAME
FR2479000A1 (en) * 1980-03-28 1981-10-02 Research Corp BRUCELLOSIS VACCINE, LIVESTOCK DISEASE
FR2534259A1 (en) * 1982-10-08 1984-04-13 Ss Pharmaceutical Co MEDIUM CHAIN ALIPHATIC ACID DIESTER IN 6,6 'POSITIONS OF A, A-TREHALOSE AND THERAPEUTIC APPLICATION THEREOF
US4574058A (en) * 1978-02-24 1986-03-04 Ciba-Geigy Corporation Antigen derivatives and processes for their preparation

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1216846A (en) * 1982-04-29 1987-01-20 Edgar E. Ribi Purification of trehalose dimycolates and product
US5049664A (en) * 1988-08-26 1991-09-17 Sawai Pharmaceutical Co., Ltd. Trehalose derivatives

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH63A (en) * 1889-01-08 Oesterr Alpine Montan Hydraulic press for the production of lead sheaths on cables and lead pipes
CH76A (en) * 1888-11-14 1889-01-09 Carnal Paul E New watch box system that can be used as a bar of soap or as an ice box
CH77A (en) * 1889-01-09 Christian Herren Root cutting machine
CH79A (en) * 1889-01-09 Adam Sautter Johann Movement for pocket watches with an open barrel, new gear pusher system and simplified movement fastening

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH63A (en) * 1889-01-08 Oesterr Alpine Montan Hydraulic press for the production of lead sheaths on cables and lead pipes
CH77A (en) * 1889-01-09 Christian Herren Root cutting machine
CH79A (en) * 1889-01-09 Adam Sautter Johann Movement for pocket watches with an open barrel, new gear pusher system and simplified movement fastening
CH76A (en) * 1888-11-14 1889-01-09 Carnal Paul E New watch box system that can be used as a bar of soap or as an ice box

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
11 DOCUMENT CITE DANS LA DEMANDE EXAMINEE *
1965 7093G, CITE CAN J. CHEM. 43 7 2004 *
1972 28 833N CITE NIPPON SAIKINGAKU ZASSHI 1971, 26 11 533-6) *
1972 81.777C CITE SCIENCE 1971, 174 4015 1240-2 *
1973 155.815T CITE BIOCHEMIE 1973 55 5 575-578 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2355506A1 (en) * 1976-06-25 1978-01-20 Azuma Ichiro IMMUNOTHERAPY ADJUVANT CONTAINING GLYCOLIPID AS ACTIVE INGREDIENT AND PROCESS FOR PREPARATION
US4574058A (en) * 1978-02-24 1986-03-04 Ciba-Geigy Corporation Antigen derivatives and processes for their preparation
EP0005682A1 (en) * 1978-05-18 1979-11-28 Ciba-Geigy Ag Silyl-glucosamine derivatives, process for their preparation and medicines containing them
WO1979001088A1 (en) * 1978-05-18 1979-12-13 Ciba Geigy Ag New glucosamin silyl compounds and preparation process thereof
FR2477551A1 (en) * 1980-03-10 1981-09-11 Anvar NEW DERIVATIVES OF A-TREHALOSE AND MEDICAMENTS CONTAINING SAME
WO1981002576A1 (en) * 1980-03-10 1981-09-17 Anvar New derivatives of 1'0alpha,0alpha'-trehalose and drugs containing them
FR2479000A1 (en) * 1980-03-28 1981-10-02 Research Corp BRUCELLOSIS VACCINE, LIVESTOCK DISEASE
FR2534259A1 (en) * 1982-10-08 1984-04-13 Ss Pharmaceutical Co MEDIUM CHAIN ALIPHATIC ACID DIESTER IN 6,6 'POSITIONS OF A, A-TREHALOSE AND THERAPEUTIC APPLICATION THEREOF

Also Published As

Publication number Publication date
BE844272A (en) 1977-01-19
FR2319373B1 (en) 1978-12-01
DE2633690A1 (en) 1977-02-17

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