(1'S,3S,4R,5S)-3-azido-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-azido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran
• CAS No.: 344615-51-6
• Molecular Formula: C₄₂H₆₃N₃O₇Si₃
• Molecular Weight: 806.235
• Mol file: 344615-51-6.mol

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (1'S,3S,4R,5S)-3-azido-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: 62.0%

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

Guidance literature:

(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; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 3h;

With pyridinium p-toluenesulfonate; In toluene; at 70 ℃; for 24h;

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

Reference yield:

2-azido-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-(2-trimethylsilanyl-ethoxymethoxy)-hexanoic acid dimethylamide (500783-42-6) → (1'S,3S,4R,5S)-3-azido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran (344615-51-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In toluene; at 70 ℃; for 24h;

DOI:10.1016/S0040-4039(01)00246-5

Reference yield: 35.0%

(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-azido-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-4-hydroxy-2-oxo-tetrahydrofuran (344615-52-7) + (3S,4R,5S)-3-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-[(S)-2-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-dihydro-furan-2-one

Guidance literature:

With sodium bromate; sodium dithionite; In ethyl acetate; at 20 ℃; for 2h;

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

upstream raw materials:

2-azido-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-(2-trimethylsilanyl-ethoxymethoxy)-hexanoic acid dimethylamide

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

(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

sphingofungin E

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