(4S,5R)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one

Base Information

• Chemical Name: (4S,5R)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one
• CAS No.: 203927-01-9
• Molecular Formula: C₂₂H₂₇N₃O₄Si
• Molecular Weight: 425.56
• Mol file: 203927-01-9.mol

Synonyms:(4S,5R)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one

Chemical Property of (4S,5R)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one

There total 7 articles about (4S,5R)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one 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: 67.0%

(3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-5-iodo-3,4-bis-trimethylsilanyloxy-hexanoic acid methyl ester (204328-43-8) → (4S,5R)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one (203927-01-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 20h;

DOI:10.1021/jo972116s

Reference yield:

(2R,3R)-4-(tert-Butyldiphenylsilyloxy)-2,3-epoxybutan-1-al (131380-35-3) → (4S,5R)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one (203927-01-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent

2: 80 percent / magnesium iodide / toluene / 19 h / -78 °C

3: 98 percent / pyridine, hexamethyldisilazane / 12 h

4: 67 percent / sodium azide / dimethylformamide / 20 h / 60 °C

With pyridine; sodium azide; 1,1,1,3,3,3-hexamethyl-disilazane; magnesium iodide; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo972116s

Reference yield:

(S)-3-[(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-oxiranyl]-3-hydroxy-propionic acid methyl ester → (4S,5R)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one (203927-01-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / magnesium iodide / toluene / 19 h / -78 °C

2: 98 percent / pyridine, hexamethyldisilazane / 12 h

3: 67 percent / sodium azide / dimethylformamide / 20 h / 60 °C

With pyridine; sodium azide; 1,1,1,3,3,3-hexamethyl-disilazane; magnesium iodide; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo972116s

upstream raw materials:

methanol

(3S,4R,5R)-tert-butyl [6-(tert-butyldiphenylsilyloxy)-4,5-epoxy-3-hydroxy]hexanoate

(3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-5-iodo-3,4-bis-trimethylsilanyloxy-hexanoic acid methyl ester

(2R,3R)-4-(tert-Butyldiphenylsilyloxy)-2,3-epoxybutan-1-al

Downstream raw materials:

(1'R,4S,5R)-5-(1'-azido-2'-tert-butyldiphenylsilyloxy)ethyl-4-benzyloxy-3,4-dihydrofuran-2(5H)-one