N-{(3S,4R,5S)-4-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5-[(R)-2-oxo-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-tetrahydro-furan-3-yl}-benzamide

Base Information

• Chemical Name: N-{(3S,4R,5S)-4-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5-[(R)-2-oxo-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-tetrahydro-furan-3-yl}-benzamide
• CAS No.: 400746-55-6
• Molecular Formula: C₄₃H₅₃NO₈Si₂
• Molecular Weight: 768.067

Synonyms:

Chemical Property of N-{(3S,4R,5S)-4-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5-[(R)-2-oxo-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-tetrahydro-furan-3-yl}-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{(3S,4R,5S)-4-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5-[(R)-2-oxo-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-tetrahydro-furan-3-yl}-benzamide

There total 6 articles about N-{(3S,4R,5S)-4-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5-[(R)-2-oxo-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-tetrahydro-furan-3-yl}-benzamide 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:

(1'S,3S,4R,5S)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[2'-hydroxy-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-2-oxo-tetrahydrofuran (400746-49-8) → N-{(3S,4R,5S)-4-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5-[(R)-2-oxo-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-tetrahydro-furan-3-yl}-benzamide (400746-55-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.5h;

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) → N-{(3S,4R,5S)-4-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5-[(R)-2-oxo-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-tetrahydro-furan-3-yl}-benzamide (400746-55-6)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 82 percent / H₂SO₄ / H₂O; acetone / 3 h / 20 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

With dmap; sulfuric acid; hydrogen; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In dichloromethane; water; ethyl acetate; acetone;

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) → N-{(3S,4R,5S)-4-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5-[(R)-2-oxo-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-tetrahydro-furan-3-yl}-benzamide (400746-55-6)

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

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

4.1: 82 percent / H₂SO₄ / H₂O; acetone / 3 h / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

With dmap; sulfuric acid; hydrogen; Dess-Martin periodane; 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

upstream 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

benzoyl chloride

(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:

(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[3'-iodo-1'-[2-(trimethylsilyl)ethoxymethoxy]prop-2'-en-1'-yl]-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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