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

Base Information

• Chemical Name: 2,3-di-O-benzyl-6-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)
• CAS No.: 869213-37-6
• Molecular Formula: C₃₉H₄₀O₈
• Molecular Weight: 636.742
• Mol file: 869213-37-6.mol

Synonyms:2,3-di-O-benzyl-6-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)

Chemical Property of 2,3-di-O-benzyl-6-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-di-O-benzyl-6-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)

There total 2 articles about 2,3-di-O-benzyl-6-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) 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:

3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (150772-61-5) → 2,3-di-O-benzyl-6-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (869213-37-6)

Guidance literature:

Multi-step reaction with 2 steps

1: TBAF / tetrahydrofuran

2: 4.16 g / pyridine; DMAP

With pyridine; dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/jo070018t

Reference yield:

benzoyl chloride (98-88-4) + ((3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-5-yl)-methanol → 2,3-di-O-benzyl-6-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (869213-37-6)

Guidance literature:

With pyridine; dmap;

DOI:10.1021/jo070018t

Reference yield: 99.0%

2,3-di-O-benzyl-6-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (869213-37-6) + (2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-(1->2)-[(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)]-1-O-allyl-3,4,5-tri-O-benzyl-D-myo-inositol → (2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-(1->2)-[(2,6-di-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-(1->6)-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)]-1-O-allyl-3,4,5-tri-O-benzyl-D-myo-inositol

Guidance literature:

With N-iodo-succinimide; scandium tris(trifluoromethanesulfonate); In dichloromethane; for 0.25h; cooling;

DOI:10.1002/anie.200500505

upstream raw materials:

benzoyl chloride

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

Downstream raw materials:

C₇₇H₈₀O₁₈

C₅₇H₅₈O₁₃

C₂₃H₂₈O₆(COC₆H₄)2

allyl 3,4-di-O-benzyl-6-O-(3,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside