Benzyl 5-deoxy-5-{(1''S,2''S,3''S,4''R)-[5''-chloro-3''-endo-methoxymethoxy-7-oxabicyclo[2.2.1]hept-5''-en-2''-endo-yl]methyl}-[(tert-butyl)dimethylsilyl]-2,3-di-O-methoxymethyl-α/β-L-gulofuranosiduronate

Base Information

Chemical Name:Benzyl 5-deoxy-5-{(1''S,2''S,3''S,4''R)-[5''-chloro-3''-endo-methoxymethoxy-7-oxabicyclo[2.2.1]hept-5''-en-2''-endo-yl]methyl}-[(tert-butyl)dimethylsilyl]-2,3-di-O-methoxymethyl-α/β-L-gulofuranosiduronate
CAS No.:245511-12-0
Molecular Formula:C₃₂H₄₉ClO₁₁Si
Molecular Weight:673.273
Hs Code.:

Benzyl 5-deoxy-5-{(1''S,2''S,3''S,4''R)-[5''-chloro-3''-endo-methoxymethoxy-7-oxabicyclo[2.2.1]hept-5''-en-2''-endo-yl]methyl}-[(tert-butyl)dimethylsilyl]-2,3-di-O-methoxymethyl-α/β-L-gulofuranosiduronate

Synonyms:Benzyl 5-deoxy-5-{(1''S,2''S,3''S,4''R)-[5''-chloro-3''-endo-methoxymethoxy-7-oxabicyclo[2.2.1]hept-5''-en-2''-endo-yl]methyl}-[(tert-butyl)dimethylsilyl]-2,3-di-O-methoxymethyl-α/β-L-gulofuranosiduronate

Suppliers and Price of Benzyl 5-deoxy-5-{(1''S,2''S,3''S,4''R)-[5''-chloro-3''-endo-methoxymethoxy-7-oxabicyclo[2.2.1]hept-5''-en-2''-endo-yl]methyl}-[(tert-butyl)dimethylsilyl]-2,3-di-O-methoxymethyl-α/β-L-gulofuranosiduronate

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Chemical Property of Benzyl 5-deoxy-5-{(1''S,2''S,3''S,4''R)-[5''-chloro-3''-endo-methoxymethoxy-7-oxabicyclo[2.2.1]hept-5''-en-2''-endo-yl]methyl}-[(tert-butyl)dimethylsilyl]-2,3-di-O-methoxymethyl-α/β-L-gulofuranosiduronate

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Technology Process of Benzyl 5-deoxy-5-{(1''S,2''S,3''S,4''R)-[5''-chloro-3''-endo-methoxymethoxy-7-oxabicyclo[2.2.1]hept-5''-en-2''-endo-yl]methyl}-[(tert-butyl)dimethylsilyl]-2,3-di-O-methoxymethyl-α/β-L-gulofuranosiduronate

There total 6 articles about Benzyl 5-deoxy-5-{(1''S,2''S,3''S,4''R)-[5''-chloro-3''-endo-methoxymethoxy-7-oxabicyclo[2.2.1]hept-5''-en-2''-endo-yl]methyl}-[(tert-butyl)dimethylsilyl]-2,3-di-O-methoxymethyl-α/β-L-gulofuranosiduronate 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: 61.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: (S)-3-((1S,2S,3S,4R)-5-Chloro-3-methoxymethoxy-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-2-((2R,3R,4S)-5-hydroxy-3,4-bis-methoxymethoxy-tetrahydro-furan-2-yl)-propionic acid benzyl ester

: 245511-12-0
Benzyl 5-deoxy-5-{(1''S,2''S,3''S,4''R)-[5''-chloro-3''-endo-methoxymethoxy-7-oxabicyclo[2.2.1]hept-5''-en-2''-endo-yl]methyl}-[(tert-butyl)dimethylsilyl]-2,3-di-O-methoxymethyl-α/β-L-gulofuranosiduronate

Guidance literature:: With 2,6-dimethylpyridine; at -15 ℃; for 1h;
DOI:10.1016/0040-4039(96)00189-X

Reference yield:

: 176540-25-3
(-)-5-Deoxy-5-{(1''S,2''S,3''S,4''R)-[5''-chloro-3''-endo-hydroxy-7-oxabicyclo[2.2.1]hept-5''-en-2''-endo-yl]methyl}-2,3-di-O-methoxymethyl-L-gulo-furanurono-6,1-lactone

: 245511-12-0
Benzyl 5-deoxy-5-{(1''S,2''S,3''S,4''R)-[5''-chloro-3''-endo-methoxymethoxy-7-oxabicyclo[2.2.1]hept-5''-en-2''-endo-yl]methyl}-[(tert-butyl)dimethylsilyl]-2,3-di-O-methoxymethyl-α/β-L-gulofuranosiduronate

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / (i-Pr)2NEt / CH₂Cl₂ / 52 h / 0 - 20 °C

2: 1.) BuLi, 2.) AcOH / 1.) THF, from 0 deg C to 15 deg C, 4 h

3: 61 percent / 2,6-lutidine / 1 h / -15 °C

With 2,6-dimethylpyridine; n-butyllithium; acetic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1016/0040-4039(96)00189-X

Reference yield:

: (1S,4S,5R,6R,7S)-4-((1S,2R,3S,4R,5S,6S)-5-Chloro-3-hydroxy-6-phenylselanyl-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl)-6,7-bis-methoxymethoxy-2,8-dioxa-bicyclo[3.2.1]octan-3-one

: 245511-12-0
Benzyl 5-deoxy-5-{(1''S,2''S,3''S,4''R)-[5''-chloro-3''-endo-methoxymethoxy-7-oxabicyclo[2.2.1]hept-5''-en-2''-endo-yl]methyl}-[(tert-butyl)dimethylsilyl]-2,3-di-O-methoxymethyl-α/β-L-gulofuranosiduronate

Guidance literature:: Multi-step reaction with 4 steps

1: m-CPBA / tetrahydrofuran; CH₂Cl₂ / 4 h / -78 - 20 °C

2: 75 percent / (i-Pr)2NEt / CH₂Cl₂ / 52 h / 0 - 20 °C

3: 1.) BuLi, 2.) AcOH / 1.) THF, from 0 deg C to 15 deg C, 4 h

4: 61 percent / 2,6-lutidine / 1 h / -15 °C

With 2,6-dimethylpyridine; n-butyllithium; acetic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0040-4039(96)00189-X