pent-4-enyl 2-O-(2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Base Information

• Chemical Name: pent-4-enyl 2-O-(2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• CAS No.: 150772-53-5
• Molecular Formula: C₇₅H₈₂O₁₂Si
• Molecular Weight: 1203.55
• Mol file: 150772-53-5.mol

Synonyms:pent-4-enyl 2-O-(2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Chemical Property of pent-4-enyl 2-O-(2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pent-4-enyl 2-O-(2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

There total 5 articles about pent-4-enyl 2-O-(2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-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: 90.0%

pent-4-enyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside (123487-56-9) + 3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (150772-61-5) → pent-4-enyl 2-O-(2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (150772-53-5)

Guidance literature:

With N-iodo-succinimide; ytterbium(III) triflate; In dichloromethane; at 0 ℃;

DOI:10.1021/ol0511981

Reference yield: 89.0%

pent-4-enyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside (123487-56-9) + Benzoic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-bromo-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester (150772-62-6) → pent-4-enyl 2-O-(2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (150772-53-5)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -30 ℃; for 0.5h;

DOI:10.1021/ja00070a048

Reference yield:

3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (125392-62-3) → pent-4-enyl 2-O-(2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (150772-53-5)

Guidance literature:

Multi-step reaction with 3 steps

1: TsOH / CH₂Cl₂ / 60 °C

2: NaOMe

3: 89 percent / AgOTf, molecular sieves 4A / CH₂Cl₂ / 0.5 h / -30 °C

With 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1021/ja00070a048

upstream raw materials:

pent-4-enyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside

Benzoic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-bromo-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester

3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)

3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)