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

Base Information

• Chemical Name: allyl 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside
• CAS No.: 225924-62-9
• Molecular Formula: C₃₉H₄₆O₆Si
• Molecular Weight: 638.876
• Mol file: 225924-62-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about allyl 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside 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: 95.0%

Allyl-2-O-acetyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsiloxan-α-D-mannopyranosid (136944-95-1) → allyl 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside (225924-62-9)

Guidance literature:

With sodium methylate; In methanol; for 6h; Ambient temperature;

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

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → allyl 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside (225924-62-9)

Guidance literature:

Multi-step reaction with 6 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

6: 95 percent / NaOMe / methanol / 6 h / Ambient temperature

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; sodium methylate; sodium hydride; acetic acid; In methanol; 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

Reference yield:

O-(2-O-acetyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl) trichloroacetimidate (220734-62-3) → allyl 3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside (225924-62-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / molecular sieves (3 Angstroem), TMSOTf / diethyl ether / 0.25 h / Ambient temperature

2: 95 percent / NaOMe / methanol / 6 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; sodium methylate; In methanol; diethyl ether;

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

upstream raw materials:

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

benzyl bromide

tert-butylchlorodiphenylsilane

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

Downstream raw materials:

allyl 2-O-allyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside

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

allyl 2-O-allyl-3,4-di-O-benzyl-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-α-D-mannopyranoside

allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2-O-allyl-3,4-di-O-benzyl-α-D-mannopyranoside