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

Base Information

• Chemical Name: p-cresyl 2-azido-2-deoxy-3,6-di-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside
• CAS No.: 172511-57-8
• Molecular Formula: C₂₅H₄₅N₃O₄SSi₂
• Molecular Weight: 539.887
• Mol file: 172511-57-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about p-cresyl 2-azido-2-deoxy-3,6-di-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside 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:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide (67673-39-6) → p-cresyl 2-azido-2-deoxy-3,6-di-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside (172511-57-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / NaOH / ethanol; CHCl₃

2: 99 percent

With sodium hydroxide; In ethanol; chloroform;

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

Reference yield:

para-thiocresol (106-45-6) → p-cresyl 2-azido-2-deoxy-3,6-di-O-tert-butyldimethylsilyl-1-thio-β-D-galactopyranoside (172511-57-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / NaOH / ethanol; CHCl₃

2: 99 percent

With sodium hydroxide; In ethanol; chloroform;

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

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

upstream raw materials:

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

para-thiocresol

Downstream raw materials:

(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

(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,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-[(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