(2S,3R,4S,5R)-5-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2,3,6-trihydroxy-hexanoic acid methyl ester

Base Information

• Chemical Name: (2S,3R,4S,5R)-5-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2,3,6-trihydroxy-hexanoic acid methyl ester
• CAS No.: 201340-26-3
• Molecular Formula: C₂₃H₃₁N₃O₆Si
• Molecular Weight: 473.601
• Mol file: 201340-26-3.mol

Synonyms:(2S,3R,4S,5R)-5-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2,3,6-trihydroxy-hexanoic acid methyl ester

Chemical Property of (2S,3R,4S,5R)-5-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2,3,6-trihydroxy-hexanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R)-5-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2,3,6-trihydroxy-hexanoic acid methyl ester

There total 4 articles about (2S,3R,4S,5R)-5-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2,3,6-trihydroxy-hexanoic acid methyl ester 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: 80.0%

(4S,5R)-5-[(1S,2R)-2-Azido-1-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-propyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester (201340-25-2) → (2S,3R,4S,5R)-5-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2,3,6-trihydroxy-hexanoic acid methyl ester (201340-26-3)

Guidance literature:

With iodine; In methanol; at 45 ℃; for 46h;

DOI:10.1021/jo971335a

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3R,4S,5R)-5-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2,3,6-trihydroxy-hexanoic acid methyl ester (201340-26-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / imidazole / tetrahydrofuran / 1.) reflux, 4 h, 2.) room temperature, 12 h

2: 1.) O₃/O₂, 2.) NaBH₄ / 1.) -78 deg C, 20 min, 2.) 0 deg C -> room temperature

3: 80 percent / I₂ / methanol / 46 h / 45 °C

With 1H-imidazole; sodium tetrahydroborate; iodine; oxygen; ozone; In tetrahydrofuran; methanol;

DOI:10.1021/jo971335a

Reference yield:

((3aR,4S,5R,7aS)-5-Azido-7-chloro-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yloxy)-tert-butyl-diphenyl-silane (201340-24-1) → (2S,3R,4S,5R)-5-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2,3,6-trihydroxy-hexanoic acid methyl ester (201340-26-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃/O₂, 2.) NaBH₄ / 1.) -78 deg C, 20 min, 2.) 0 deg C -> room temperature

2: 80 percent / I₂ / methanol / 46 h / 45 °C

With sodium tetrahydroborate; iodine; oxygen; ozone; In methanol;

DOI:10.1021/jo971335a

upstream raw materials:

(4S,5R)-5-[(1S,2R)-2-Azido-1-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-propyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

tert-butylchlorodiphenylsilane

((3aR,4S,5R,7aS)-5-Azido-7-chloro-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yloxy)-tert-butyl-diphenyl-silane