(1'S,3S,4R,5S)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[2'-hydroxy-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-2-oxo-tetrahydrofuran

Base Information

Chemical Name:(1'S,3S,4R,5S)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[2'-hydroxy-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-2-oxo-tetrahydrofuran
CAS No.:344615-54-9
Molecular Formula:C₄₃H₅₃NO₉Si₂
Molecular Weight:784.066
Hs Code.:

(1'S,3S,4R,5S)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[2'-hydroxy-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-2-oxo-tetrahydrofuran

Synonyms:(1'S,3S,4R,5S)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[2'-hydroxy-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-2-oxo-tetrahydrofuran

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Chemical Property of (1'S,3S,4R,5S)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[2'-hydroxy-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-2-oxo-tetrahydrofuran

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Technology Process of (1'S,3S,4R,5S)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[2'-hydroxy-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-2-oxo-tetrahydrofuran

There total 8 articles about (1'S,3S,4R,5S)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[2'-hydroxy-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-2-oxo-tetrahydrofuran 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: 87.0%

: 344615-53-8
(1'S,3S,4R,5S)-3-benzamido-4-benzoyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran

: 344615-54-9
(1'S,3S,4R,5S)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[2'-hydroxy-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-2-oxo-tetrahydrofuran

Guidance literature:: With sulfuric acid; In acetone; at 20 ℃; for 13h;
DOI:10.1016/S0040-4039(01)00246-5

Reference yield:

: 344615-51-6
(1'S,3S,4R,5S)-3-azido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran

: 344615-54-9
(1'S,3S,4R,5S)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[2'-hydroxy-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-2-oxo-tetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1: 61 percent / NaBrO₃; NaHSO₃ / ethyl acetate; H₂O / 1 h / 20 °C

2: H₂ / Pd/C / ethyl acetate / 14 h / 20 °C

3: 0.24 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 2 h / 20 °C

4: 87 percent / H₂SO₄ / H₂O; acetone / 13 h / 20 °C

With dmap; sodium bromate; sulfuric acid; hydrogen; sodium hydrogensulfite; triethylamine; palladium on activated charcoal; In dichloromethane; water; ethyl acetate; acetone;
DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

: 344615-50-5
(2S,3R,4R,5S)-N,N-dimethyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-4-(p-methoxybenzyloxy)-5-[2-(trimethylsilyl)ethoxymethoxy]hexanoamide

: 344615-54-9
(1'S,3S,4R,5S)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[2'-hydroxy-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-2-oxo-tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 3 h / 20 °C

1.2: 62 percent / pyridinium p-toluenesulfonate / toluene / 24 h / 70 °C

2.1: 61 percent / NaBrO₃; NaHSO₃ / ethyl acetate; H₂O / 1 h / 20 °C

3.1: H₂ / Pd/C / ethyl acetate / 14 h / 20 °C

4.1: 0.24 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 2 h / 20 °C

5.1: 87 percent / H₂SO₄ / H₂O; acetone / 13 h / 20 °C

With dmap; sodium bromate; sulfuric acid; hydrogen; sodium hydrogensulfite; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In dichloromethane; water; ethyl acetate; acetone;
DOI:10.1016/S0040-4020(02)01058-X