Acetic acid (2R,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R,3R,4S)-3-benzyloxy-5-chloro-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R,3R,4S)-3-benzyloxy-5-chloro-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-tetrahydro-pyran-3-yl ester
CAS No.:139426-64-5
Molecular Formula:C₂₈H₃₃ClO₁₁
Molecular Weight:581.016
Hs Code.:

Acetic acid (2R,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R,3R,4S)-3-benzyloxy-5-chloro-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-tetrahydro-pyran-3-yl ester

Synonyms:Acetic acid (2R,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R,3R,4S)-3-benzyloxy-5-chloro-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R,3R,4S)-3-benzyloxy-5-chloro-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R,3R,4S)-3-benzyloxy-5-chloro-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-tetrahydro-pyran-3-yl ester

There total 3 articles about Acetic acid (2R,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R,3R,4S)-3-benzyloxy-5-chloro-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-tetrahydro-pyran-3-yl 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: 25.0%

: 100-39-0
benzyl bromide

: 134160-54-6
(+)-(1S,3R,4R,5R,6R)-6-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>hept-5-en-2-endo-ol

: 139426-64-5
Acetic acid (2R,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R,3R,4S)-3-benzyloxy-5-chloro-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1021/jo00033a032

Reference yield:

: 134160-53-5
(+)-(1S,3R,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-endo-ol

: 139426-64-5
Acetic acid (2R,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R,3R,4S)-3-benzyloxy-5-chloro-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 96.6 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 2.25 h / -78 °C

2: 25 percent / NaH / dimethylformamide

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00033a032

Reference yield:

: 134160-52-4
(+)-(1S,3R,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-<(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)methyl>-7-oxabicyclo<2.2.1>heptan-2-one

: 139426-64-5
Acetic acid (2R,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R,3R,4S)-3-benzyloxy-5-chloro-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 99.7 percent / NaBH₄ / tetrahydrofuran; methanol / 0.17 h / 0 °C

2: 96.6 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 2.25 h / -78 °C

3: 25 percent / NaH / dimethylformamide

With sodium tetrahydroborate; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00033a032