(R)-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-O-glycerol

Base Information

• Chemical Name: (R)-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-O-glycerol
• CAS No.: 132928-95-1
• Molecular Formula: C₃₆H₅₅NO₁₅Si
• Molecular Weight: 769.916
• Mol file: 132928-95-1.mol

Synonyms:

Chemical Property of (R)-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-O-glycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-O-glycerol

There total 8 articles about (R)-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-O-glycerol 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: 11.2%

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) + (R)-2-O-benzyl-1-O-tert-butyldimethylsilylglycerol (132928-94-0) → (R)-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-O-glycerol (132928-95-1,132928-96-2) + (R)-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-O-glycerol (132928-95-1,132928-96-2)

Guidance literature:

With 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; In dichloromethane; for 96h; Ambient temperature;

DOI:10.1248/cpb.38.3347

Reference yield: 11.2%

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) + (R)-2-O-benzyl-1-O-tert-butyldimethylsilylglycerol (132928-94-0) → (R)-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-O-glycerol (132928-95-1,132928-96-2) + (R)-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-O-glycerol (132928-95-1,132928-96-2)

Guidance literature:

With 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; In dichloromethane; for 96h; Ambient temperature;

DOI:10.1248/cpb.38.3347

Reference yield:

(S)-2-(benzyloxy)-3-hydroxypropyl acetate (109429-01-8) → (R)-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-O-glycerol (132928-95-1,132928-96-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / triethylamine / CH₂Cl₂ / 3 h / Ambient temperature

2: 92.7 percent / KOH / methanol / 15 h / Ambient temperature

3: 8.8 percent / Hg(CN)2, HgBr₂, molecular sieves 4A / CH₂Cl₂ / 96 h / Ambient temperature

With potassium hydroxide; 4 A molecular sieve; mercury(II) cyanide; triethylamine; mercury dibromide; In methanol; dichloromethane;

DOI:10.1248/cpb.38.3347

upstream raw materials:

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

(R)-2-O-benzyl-1-O-tert-butyldimethylsilylglycerol

(S)-2-(benzyloxy)-3-hydroxypropyl acetate

(R)-1-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilylglycerol