(Z)-2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

Base Information

• Chemical Name: (Z)-2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride
• CAS No.: 451463-10-8
• Molecular Formula: C₃₀H₃₃FO₅
• Molecular Weight: 492.587
• Mol file: 451463-10-8.mol

Synonyms:(Z)-2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

Chemical Property of (Z)-2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

There total 3 articles about (Z)-2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride 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:

2-O-allyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride (358351-60-7) → (Z)-2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride (451463-10-8) + (E)-2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

Guidance literature:

With n-butyllithium; Wilkinson's catalyst; In tetrahydrofuran; hexane; at 70 ℃; for 0.75h; Title compound not separated from byproducts;

DOI:10.1007/s007060200020

Reference yield:

3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose (158852-31-4) → (Z)-2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride (451463-10-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / (diethylamino)-sulfur trifluoride / CH₂Cl₂ / 7.5 h / 0 °C

2: 93 percent / NaH / dimethylformamide / 1 h / 0 °C

3: n-BuLi / Wilkinson's catalyst / tetrahydrofuran; hexane / 0.75 h / 70 °C

With n-butyllithium; diethylamino-sulfur trifluoride; sodium hydride; Wilkinson's catalyst; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1007/s007060200020

Reference yield:

2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride (194807-96-0) → (Z)-2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride (451463-10-8)

Guidance literature:

Multi-step reaction with 3 steps

1: n-propylamine / methanol; tetrahydrofuran / 45 °C

2: 93 percent / NaH / dimethylformamide / 0 °C

3: BuLi; Wilkinson's catalyst / tetrahydrofuran / 70 °C

With propylamine; Wilkinson's catalyst; n-butyllithium; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ol016175a

upstream raw materials:

2-O-allyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose

2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

Downstream raw materials:

2-O-(2-iodo-1-methoxypropyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

2-O-(2-iodo-1-(methyl-2,3,4-tri-O-benzyl-α-D-mannopyranosid-6-O-yl)-propyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

2-O-(2-iodo-1-(methyl-2-O-benzyl-4-6-O-benzylidene-α-D-mannopyranosid-3-O-yl)-propyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

2-O-(1-cyclohexyloxy-2-iodopropyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride