(2S,3R)-3-[(3R,4R,5S,6R)-3-Azido-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

Base Information

• Chemical Name: (2S,3R)-3-[(3R,4R,5S,6R)-3-Azido-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester
• CAS No.: 186599-83-7
• Molecular Formula: C₄₄H₆₂N₄O₉Si₂
• Molecular Weight: 847.169
• Mol file: 186599-83-7.mol

Synonyms:(2S,3R)-3-[(3R,4R,5S,6R)-3-Azido-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

Chemical Property of (2S,3R)-3-[(3R,4R,5S,6R)-3-Azido-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-[(3R,4R,5S,6R)-3-Azido-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

There total 4 articles about (2S,3R)-3-[(3R,4R,5S,6R)-3-Azido-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl 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: 71.0%

N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester (73724-48-8) + p-cresyl 2-azido-2-deoxy-3,6-di-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside (172511-57-8) → (2S,3R)-3-[(3R,4R,5S,6R)-3-Azido-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester (186599-83-7)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane;

DOI:10.1016/0040-4039(95)01515-9

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide (67673-39-6) → (2S,3R)-3-[(3R,4R,5S,6R)-3-Azido-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester (186599-83-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / NaOH / ethanol; CHCl₃

2: 99 percent

3: 71 percent / NBS/QOTf / CH₂Cl₂

With sodium hydroxide; N-Bromosuccinimide; In ethanol; dichloromethane; chloroform;

DOI:10.1016/0040-4039(95)01515-9

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3R)-3-[(3R,4R,5S,6R)-3-Azido-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester (186599-83-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent

2: 71 percent / NBS/QOTf / CH₂Cl₂

With N-Bromosuccinimide; In dichloromethane;

DOI:10.1016/0040-4039(95)01515-9

upstream raw materials:

N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester

p-cresyl 2-azido-2-deoxy-3,6-di-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside

3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide

tert-butyldimethylsilyl chloride

Downstream raw materials:

C₅₇H₆₉N₃O₂₂

(2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Acetylamino-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

(2S,3R)-3-[(2S,3R,4R,5S,6R)-3-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester