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

Base Information

• Chemical Name: allyl 3-O-benzyl-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-2-O-levulinyl-α-D-mannopyranoside
• CAS No.: 1351452-37-3
• Molecular Formula: C₄₈H₅₄O₈Si
• Molecular Weight: 787.037
• Mol file: 1351452-37-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about allyl 3-O-benzyl-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-2-O-levulinyl-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 3-O-benzyl-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside (1351452-36-2) + levulinic acid (123-76-2) → allyl 3-O-benzyl-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-2-O-levulinyl-α-D-mannopyranoside (1351452-37-3)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In dichloromethane; for 4h; Inert atmosphere;

DOI:10.1002/anie.201103483

Reference yield:

2-bromomethylnaphthyl bromide (939-26-4) → allyl 3-O-benzyl-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-2-O-levulinyl-α-D-mannopyranoside (1351452-37-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 h / 0 °C / Inert atmosphere

2.1: water; acetic acid / chloroform / 4 h / 50 - 65 °C / Inert atmosphere

3.1: di(n-butyl)tin oxide / toluene / 4 h / Reflux; Inert atmosphere

3.2: 1 h / Inert atmosphere

4.1: dmap; diisopropyl-carbodiimide / dichloromethane / 4 h / Inert atmosphere

With dmap; water; sodium hydride; di(n-butyl)tin oxide; acetic acid; diisopropyl-carbodiimide; In dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1002/anie.201103483

Reference yield:

allyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside (1055301-74-0) → allyl 3-O-benzyl-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-2-O-levulinyl-α-D-mannopyranoside (1351452-37-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 h / 0 °C / Inert atmosphere

2.1: water; acetic acid / chloroform / 4 h / 50 - 65 °C / Inert atmosphere

3.1: di(n-butyl)tin oxide / toluene / 4 h / Reflux; Inert atmosphere

3.2: 1 h / Inert atmosphere

4.1: dmap; diisopropyl-carbodiimide / dichloromethane / 4 h / Inert atmosphere

With dmap; water; sodium hydride; di(n-butyl)tin oxide; acetic acid; diisopropyl-carbodiimide; In dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1002/anie.201103483

upstream raw materials:

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

allyl 2,3-O-isopropylidene-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

levulinic acid

Downstream raw materials:

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

C₃₂H₃₆O₈