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

Base Information

• Chemical Name: Allyl-2-O-acetyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsiloxan-α-D-mannopyranosid
• CAS No.: 136944-95-1
• Molecular Formula: C₄₁H₄₈O₇Si
• Molecular Weight: 680.913
• Mol file: 136944-95-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about Allyl-2-O-acetyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsiloxan-α-D-mannopyranosid 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: 97.0%

1,2-O-(Allyloxyethyliden)-3,4-di-O-benzyl-6-O-tert-butyldiphenylsiloxan-β-D-mannopyranose (136944-94-0) → Allyl-2-O-acetyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsiloxan-α-D-mannopyranosid (136944-95-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/0008-6215(92)84169-S

Reference yield: 95.0%

allyl alcohol (107-18-6) + O-(2-O-acetyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl) trichloroacetimidate (220734-62-3) → Allyl-2-O-acetyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsiloxan-α-D-mannopyranosid (136944-95-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether;

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → Allyl-2-O-acetyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsiloxan-α-D-mannopyranosid (136944-95-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 64 percent / imidazole / dimethylformamide / 24 h / 4 °C

2: 79 percent / NaH / dimethylformamide / Ambient temperature

3: AcOH / H₂O; acetone / 1 h / Ambient temperature

5: 94 percent / molecular sieves (3 Angstroem), TMSOTf / diethyl ether / 0.25 h / Ambient temperature

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; sodium hydride; acetic acid; In diethyl ether; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1153::AID-EJOC1153>3.0.CO;2-S

upstream raw materials:

1,2-O-(Allyloxyethyliden)-3,4-di-O-benzyl-6-O-tert-butyldiphenylsiloxan-β-D-mannopyranose

allyl alcohol

O-(2-O-acetyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl) trichloroacetimidate

benzyl bromide

Downstream raw materials:

Allyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-<(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranosid

O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-<(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranose

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

Allyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-O-<3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranosid