(3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2R,3R,4S)-5-chloro-3-hydroxy-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester

Base Information

Chemical Name:(3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2R,3R,4S)-5-chloro-3-hydroxy-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester
CAS No.:193409-90-4
Molecular Formula:C₃₁H₃₆ClNO₈
Molecular Weight:586.082
Hs Code.:

(3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2R,3R,4S)-5-chloro-3-hydroxy-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester

Synonyms:(3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2R,3R,4S)-5-chloro-3-hydroxy-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester

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Chemical Property of (3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2R,3R,4S)-5-chloro-3-hydroxy-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester

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Technology Process of (3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2R,3R,4S)-5-chloro-3-hydroxy-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester

There total 10 articles about (3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2R,3R,4S)-5-chloro-3-hydroxy-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

: (3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2R,3R,4S,5R,6R)-5-chloro-3-hydroxy-6-phenylselanyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester

: 193409-90-4
(3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2R,3R,4S)-5-chloro-3-hydroxy-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1) -78 deg C, 3 h; 2) -78 --> 20 deg C, 10 h;
DOI:10.1021/jo970151t

Reference yield:

: 100-39-0
benzyl bromide

: 193409-90-4
(3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2R,3R,4S)-5-chloro-3-hydroxy-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 79 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 15 h

2: 97 percent / NaHCO₃ / aq. ethanol / 2 h / 20 °C

3: 94 percent / NaIO₄ / acetic acid; H₂O / 20 °C

4: 1.) Li(SiMe₃)2 / 1) hexane, THF, -78 deg C, 50 min; 2) hexane, THF, -95 deg C, 3.5 h

5: 96 percent / NaBH₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

6: 95 percent / mCPBA / CH₂Cl₂ / 1) -78 deg C, 3 h; 2) -78 --> 20 deg C, 10 h

With sodium tetrahydroborate; sodium periodate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid;
DOI:10.1021/jo970151t

Reference yield:

: 174782-39-9
(3aS,4R,6R,7S,7aR)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol

: 193409-90-4
(3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-[(S)-((1R,2R,3R,4S)-5-chloro-3-hydroxy-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-hydroxy-methyl]-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 79 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 15 h

2: 97 percent / NaHCO₃ / aq. ethanol / 2 h / 20 °C

3: 94 percent / NaIO₄ / acetic acid; H₂O / 20 °C

4: 1.) Li(SiMe₃)2 / 1) hexane, THF, -78 deg C, 50 min; 2) hexane, THF, -95 deg C, 3.5 h

5: 96 percent / NaBH₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

6: 95 percent / mCPBA / CH₂Cl₂ / 1) -78 deg C, 3 h; 2) -78 --> 20 deg C, 10 h

With sodium tetrahydroborate; sodium periodate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid;
DOI:10.1021/jo970151t