ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside

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Chemical Name:ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside
CAS No.:1415590-66-7
Molecular Formula:C₂₈H₄₂O₄SSi
Molecular Weight:502.791
Hs Code.:

Synonyms:ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside

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Chemical Property of ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside

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Technology Process of ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside

There total 4 articles about ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside 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: 81.0%

: 1415590-65-6
ethyl 4-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside

: 100-39-0
benzyl bromide

: 1415590-66-7
ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 1.5h;
DOI:10.1021/ja307355n

Reference yield:

: 152488-30-7
ethyl 2,3-O-isopropylidene-1-thio-β-L-rhamnopyranoside

: 1415590-66-7
ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

1.2: 0.25 h / -78 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane; water / 0.5 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 20 °C

With 2,6-dimethylpyridine; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/ja307355n

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 1415590-66-7
ethyl 2,4-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

1.2: 0.25 h / -78 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane; water / 0.5 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 20 °C

With 2,6-dimethylpyridine; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/ja307355n