allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside

Base Information

• Chemical Name: allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside
• CAS No.: 1351452-34-0
• Molecular Formula: C₃₉H₄₆O₆Si
• Molecular Weight: 638.876
• Mol file: 1351452-34-0.mol

Synonyms:allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside

Chemical Property of allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside

There total 4 articles about allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-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 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside (1055301-74-0) + 2-bromomethylnaphthyl bromide (939-26-4) → allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside (1351452-34-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 5h; Inert atmosphere;

DOI:10.1002/anie.201103483

Reference yield:

allyl 6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside (182187-95-7) → allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside (1351452-34-0)

Guidance literature:

Multi-step reaction with 2 steps

1: camphor-10-sulfonic acid / acetone / 2 h / 20 °C / Inert atmosphere

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C / Inert atmosphere

With camphor-10-sulfonic acid; sodium hydride; In N,N-dimethyl-formamide; acetone; mineral oil;

DOI:10.1021/jacs.0c08583

Reference yield:

allyl α-D-mannopyranoside (41308-76-3,821794-45-0) → allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside (1351452-34-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 0 - 20 °C

2: camphor-10-sulfonic acid / acetone / 2 h / 20 °C / Inert atmosphere

3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; camphor-10-sulfonic acid; sodium hydride; In N,N-dimethyl-formamide; acetone; mineral oil;

DOI:10.1021/jacs.0c08583

upstream raw materials:

allyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside

2-bromomethylnaphthyl bromide

allyl 6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside

D-Mannose

Downstream raw materials:

allyl 3-O-benzyl-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-2-O-levulinyl-α-D-mannopyranoside

allyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinyl-α-D-mannopyranoside

allyl 4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside

allyl 3-O-benzyl-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside