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

Base Information

• Chemical Name: (1'S,3S,4R,5S)-3-benzamido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran
• CAS No.: 400746-44-3
• Molecular Formula: C₄₉H₆₉NO₈Si₃
• Molecular Weight: 884.345

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

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

There total 3 articles about (1'S,3S,4R,5S)-3-benzamido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-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: 0.21%

benzoyl chloride (98-88-4) + (3S,4R,5S)-3-Amino-4-benzyloxy-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-3-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-2-one (400746-39-6) → (1'S,3S,4R,5S)-3-benzamido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran (400746-44-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

(1'S,3S,4R,5S)-3-azido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran (344615-51-6) → (1'S,3S,4R,5S)-3-benzamido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran (400746-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

2: 0.21 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 20 °C

With dmap; hydrogen; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

(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 (344615-50-5) → (1'S,3S,4R,5S)-3-benzamido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran (400746-44-3)

Guidance literature:

Multi-step reaction with 3 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: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

3.1: 0.21 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 20 °C

With dmap; hydrogen; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In dichloromethane; water; ethyl acetate;

DOI:10.1016/S0040-4020(02)01058-X

upstream raw materials:

benzoyl chloride

(3S,4R,5S)-3-Amino-4-benzyloxy-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-3-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-2-one

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

(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

Downstream raw materials:

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

(2'E,1'S,3S,4R,5R)-3-benzamido-4-hydroxy-3-hydroxymethyl-5-(1'-hydroxy-10'-oxo-hexadec-2'-en-1'-yl)-2-oxo-tetrahydrofuran

(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-hydroxymethyl-5-(1'-hydroxy-10'-oxo-hexadec-2'-en-1'-yl)-2-oxo-tetrahydrofuran

(E)-(2S,3R,4R,5S)-2-Benzoylamino-3-benzyloxy-4,5-dihydroxy-2-hydroxymethyl-14-oxo-icos-6-enoic acid

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