JPH034558B2 - - Google Patents
Info
- Publication number
- JPH034558B2 JPH034558B2 JP59108607A JP10860784A JPH034558B2 JP H034558 B2 JPH034558 B2 JP H034558B2 JP 59108607 A JP59108607 A JP 59108607A JP 10860784 A JP10860784 A JP 10860784A JP H034558 B2 JPH034558 B2 JP H034558B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- type protecting
- protecting groups
- acetal
- solvent
- 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.)
- Expired - Lifetime
Links
- 125000006239 protecting group Chemical group 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- -1 t-butyldimethylsilyl group Chemical group 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- 150000001241 acetals Chemical class 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000010511 deprotection reaction Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 150000003180 prostaglandins Chemical class 0.000 description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- DBFKYLCYAQNIQL-UHFFFAOYSA-N 10-[tert-butyl(dimethyl)silyl]oxydecan-1-ol Chemical compound CC(C)(C)[Si](C)(C)OCCCCCCCCCCO DBFKYLCYAQNIQL-UHFFFAOYSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 1
- YFLNKMDUUCRCSU-UHFFFAOYSA-N 4-(2-hydroxyethyl)azetidin-2-one Chemical compound OCCC1CC(=O)N1 YFLNKMDUUCRCSU-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- LPEMABONSOSYTH-UHFFFAOYSA-N tert-butyl-[10-(1-ethoxyethoxy)decoxy]-dimethylsilane Chemical compound CCOC(C)OCCCCCCCCCCO[Si](C)(C)C(C)(C)C LPEMABONSOSYTH-UHFFFAOYSA-N 0.000 description 1
- KAGGHTQRAMRZLZ-UHFFFAOYSA-N tert-butyl-dimethyl-[10-(oxan-2-yloxy)decoxy]silane Chemical compound CC(C)(C)[Si](C)(C)OCCCCCCCCCCOC1CCCCO1 KAGGHTQRAMRZLZ-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59108607A JPS60255797A (ja) | 1984-05-30 | 1984-05-30 | アセタ−ル型保護基の選択的脱保護法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59108607A JPS60255797A (ja) | 1984-05-30 | 1984-05-30 | アセタ−ル型保護基の選択的脱保護法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60255797A JPS60255797A (ja) | 1985-12-17 |
| JPH034558B2 true JPH034558B2 (de) | 1991-01-23 |
Family
ID=14489083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59108607A Granted JPS60255797A (ja) | 1984-05-30 | 1984-05-30 | アセタ−ル型保護基の選択的脱保護法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60255797A (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7122615B1 (en) | 1998-09-10 | 2006-10-17 | Rutgers, The State University Of New Jersey | Polyanhydrides with therapeutically useful degradation products |
| US20040038948A1 (en) | 1999-12-07 | 2004-02-26 | Uhrich Kathryn E. | Therapeutic compositions and methods |
-
1984
- 1984-05-30 JP JP59108607A patent/JPS60255797A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60255797A (ja) | 1985-12-17 |
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