JPH024234B2 - - Google Patents
Info
- Publication number
- JPH024234B2 JPH024234B2 JP57040171A JP4017182A JPH024234B2 JP H024234 B2 JPH024234 B2 JP H024234B2 JP 57040171 A JP57040171 A JP 57040171A JP 4017182 A JP4017182 A JP 4017182A JP H024234 B2 JPH024234 B2 JP H024234B2
- Authority
- JP
- Japan
- Prior art keywords
- glucofuranose
- isopropylidene
- benzyl
- equivalents
- reaction
- 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
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 20
- 229940073608 benzyl chloride Drugs 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 13
- BGGCXQKYCBBHAH-OZRXBMAMSA-N (1r)-1-[(3ar,5r,6s,6ar)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol Chemical compound O1[C@H]([C@H](O)CO)[C@H](O)[C@H]2OC(C)(C)O[C@H]21 BGGCXQKYCBBHAH-OZRXBMAMSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- AVVWPBAENSWJCB-IVMDWMLBSA-N D-glucofuranose Chemical compound OC[C@@H](O)[C@H]1OC(O)[C@H](O)[C@H]1O AVVWPBAENSWJCB-IVMDWMLBSA-N 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 3
- 238000005574 benzylation reaction Methods 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- RNPMTPOOMRPILB-XYPQWYOHSA-N (3ar,5r,6s,6ar)-5-[(1r)-1,2-bis(phenylmethoxy)ethyl]-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole Chemical compound C([C@H]([C@H]1O[C@@H]2OC(O[C@@H]2[C@H]1OCC=1C=CC=CC=1)(C)C)OCC=1C=CC=CC=1)OCC1=CC=CC=C1 RNPMTPOOMRPILB-XYPQWYOHSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- AVVWPBAENSWJCB-UKFBFLRUSA-N alpha-D-glucofuranose Chemical compound OC[C@@H](O)[C@H]1O[C@H](O)[C@H](O)[C@H]1O AVVWPBAENSWJCB-UKFBFLRUSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- -1 dibenzyl compound Chemical class 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ULLNJSBQMBKOJH-VIVFLBMVSA-N (3R,4R,5R)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-2-ethoxy-4-phenylmethoxy-3-oxolanol Chemical compound C([C@H]([C@H]1OC([C@@H]([C@H]1OCC=1C=CC=CC=1)O)OCC)OCC=1C=CC=CC=1)OCC1=CC=CC=C1 ULLNJSBQMBKOJH-VIVFLBMVSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4017182A JPS58157797A (ja) | 1982-03-16 | 1982-03-16 | ３，５，６−トリ−Ｏ−ベンジル−１，２−Ｏ−イソプロピリデン−α−Ｄ−グルコフラノ−スの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4017182A JPS58157797A (ja) | 1982-03-16 | 1982-03-16 | ３，５，６−トリ−Ｏ−ベンジル−１，２−Ｏ−イソプロピリデン−α−Ｄ−グルコフラノ−スの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58157797A JPS58157797A (ja) | 1983-09-19 |
| JPH024234B2 true JPH024234B2 (da) | 1990-01-26 |
Family
ID=12573314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4017182A Granted JPS58157797A (ja) | 1982-03-16 | 1982-03-16 | ３，５，６−トリ−Ｏ−ベンジル−１，２−Ｏ−イソプロピリデン−α−Ｄ−グルコフラノ−スの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58157797A (da) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104478955A (zh) * | 2014-12-09 | 2015-04-01 | 济南卡博唐生物科技有限公司 | 一种3,5,6-三-氧-苄基-1,2-异丙叉基-d-葡萄糖的制备方法 |
| CN104387428A (zh) * | 2014-12-09 | 2015-03-04 | 济南卡博唐生物科技有限公司 | 一种制备3,5,6-三-氧-苄基-1,2-异丙叉基-d-葡萄糖的方法 |
-
1982
- 1982-03-16 JP JP4017182A patent/JPS58157797A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58157797A (ja) | 1983-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU620206A3 (ru) | Способ получени производных оксима или их солей | |
| JPH024234B2 (da) | ||
| JPH05112588A (ja) | アシルアミノメタンホスホン酸の製造方法 | |
| JPH0475224B2 (da) | ||
| JP4031536B2 (ja) | １，２−ジアシル−２−ｔ−アルキルヒドラジンの製造方法 | |
| JP2815654B2 (ja) | 新規な４―置換―３，５―ジメチルピコリン酸化合物およびその製造方法 | |
| JP3184345B2 (ja) | ５−クロロオキシインドールの製造方法 | |
| JP2590436B2 (ja) | ジフェニルジスルホニルフルオライドの合成方法 | |
| JP2561480B2 (ja) | ４，６−ジアルコキシ−２−アルキルチオピリミジン類の製造方法 | |
| JP2716243B2 (ja) | Ｎ―ベンジル―３―ヒドロキシスクシンアミド酸およびその製造法 | |
| JPS6026395B2 (ja) | Ｎ−トリアルキルシリルメチル尿素の合成法 | |
| KR100407720B1 (ko) | Ｎ-[3-｛3-（1-피페리디닐메틸）페녹시｝프로필]아세톡시아세트아미드의 제조방법 | |
| JP2022529000A (ja) | 置換２－［２－（フェニル）エチルアミノ］アルカンアミド誘導体の製造方法 | |
| SU829624A1 (ru) | Способ получени , -ди-трет.-буТилгидРАзОдифОРМиАТА | |
| SU608799A1 (ru) | Способ получени гидрохлорида диметилового эфира иминодипропионовой кислоты | |
| KR820001386B1 (ko) | 치환 이미다졸의 제조방법 | |
| JPH0725790B2 (ja) | ステロイド誘導体の製造方法 | |
| KR0129115B1 (ko) | 3-브로모캠퍼의 제조방법 | |
| KR100607027B1 (ko) | 아연 금속의 새로운 활성화 방법 | |
| JP2526413B2 (ja) | アルキレンジフェニルジスルホニルフルオライドおよびその合成方法 | |
| JPS5976087A (ja) | セフアロスポリン誘導体の製造方法 | |
| JPH03190856A (ja) | 精製ヒドロペルオキシドの製造方法 | |
| JPH1180151A (ja) | オキセパン−２−オン誘導体の製造方法 | |
| JPH08151405A (ja) | チーグラーナッタ触媒の電子供与性化合物として有効なエステル化合物の製造方法 | |
| JPH0120150B2 (da) |