6-O-tert-Butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose

Base Information

• Chemical Name: 6-O-tert-Butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose
• CAS No.: 163523-17-9
• Molecular Formula: C₂₅H₃₄O₇Si
• Molecular Weight: 474.626
• Mol file: 163523-17-9.mol

Synonyms:6-O-tert-Butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose

Chemical Property of 6-O-tert-Butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-tert-Butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose

There total 2 articles about 6-O-tert-Butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose 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: 70.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (29073-91-4,55865-04-8,138196-19-7) → 6-O-tert-Butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose (163523-17-9)

Guidance literature:

With 1H-imidazole;

Reference yield:

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0) → 6-O-tert-Butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose (163523-17-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium methylate / methanol / 20 °C / Inert atmosphere

1.2: Amberlyst H⁺ resin / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / Inert atmosphere

With 1H-imidazole; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/chem.201102545

Reference yield: 79.0%

benzyl bromide (100-39-0) + 6-O-tert-Butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose (163523-17-9) → 3,4-Di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose (163523-19-1)

Guidance literature:

With sodium hydride;

upstream raw materials:

tert-butylchlorodiphenylsilane

1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

Downstream raw materials:

3,4-Di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose

Allyl-2-O-acetyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsiloxan-α-D-mannopyranosid

allyl 2-O-allyl-3,4-di-O-benzyl-α-D-mannopyranoside

allyl 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside