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

Base Information

• Chemical Name: 3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)
• CAS No.: 150772-61-5
• Molecular Formula: C₄₈H₅₄O₇Si
• Molecular Weight: 771.038
• Mol file: 150772-61-5.mol

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

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

There total 3 articles about 3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-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:

3,4,6-tri-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (123487-55-8) → 3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (150772-61-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaOMe / CH₂Cl₂; methanol / 2 h

2.1: Et₃N; DMAP / CH₂Cl₂ / 12 h

2.2: NaH; TBAI / dimethylformamide / 1 h

With dmap; sodium methylate; triethylamine; In methanol; dichloromethane;

Reference yield:

benzyl bromide (100-39-0) + (3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (870101-07-8) → 3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (150772-61-5)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; Yield given. Multistep reaction; 1.) THF, 0 deg C, 15 min, 2.) THF, RT, 14 h;

DOI:10.1021/ja00110a010

Reference yield:

benzyl bromide (100-39-0) + (3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (163039-18-7) + tert-butylchlorodiphenylsilane (58479-61-1) → 3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (150772-61-5)

Guidance literature:

(3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol; tert-butylchlorodiphenylsilane; With dmap; triethylamine; In dichloromethane; for 12h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; for 1h;

upstream raw materials:

benzyl bromide

(3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

(3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

tert-butylchlorodiphenylsilane

Downstream raw materials:

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

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

tert-Butyl-diphenyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane

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