methyl 2-O-benzyl-4-deoxy-4-C-methylene-β-L-threo-pentopyranoside

Base Information

• Chemical Name: methyl 2-O-benzyl-4-deoxy-4-C-methylene-β-L-threo-pentopyranoside
• CAS No.: 848842-34-2
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.295
• Mol file: 848842-34-2.mol

Synonyms:methyl 2-O-benzyl-4-deoxy-4-C-methylene-β-L-threo-pentopyranoside

Chemical Property of methyl 2-O-benzyl-4-deoxy-4-C-methylene-β-L-threo-pentopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-benzyl-4-deoxy-4-C-methylene-β-L-threo-pentopyranoside

There total 4 articles about methyl 2-O-benzyl-4-deoxy-4-C-methylene-β-L-threo-pentopyranoside 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: 61.0%

methyl 3-O-allyl-2-O-benzyl-4-deoxy-4-C-methylene-β-L-threo-pentopyranoside (848842-33-1) → methyl 2-O-benzyl-4-deoxy-4-C-methylene-β-L-threo-pentopyranoside (848842-34-2)

Guidance literature:

With toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; Heating;

DOI:10.1016/j.tetasy.2004.12.001

Reference yield:

methyl 2-O-benzyl-3,4-O-isopropylidene-β-L-arabinopyranoside → methyl 2-O-benzyl-4-deoxy-4-C-methylene-β-L-threo-pentopyranoside (848842-34-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic acid; water / 20 °C

1.2: dibutyltin oxide / toluene / Heating

1.3: 45 percent / caesium fluoride / dimethylformamide / 20 °C

2.1: 56 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -40 - 20 °C

3.1: n-butyllithium / diethyl ether; hexane / 1 h / 20 °C

3.2: 40 percent / diethyl ether; hexane

4.1: 61 percent / 4-toluenesulfonic acid / palladium/charcoal / methanol / Heating

With n-butyllithium; oxalyl dichloride; water; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In methanol; diethyl ether; hexane; dichloromethane; 2.1: Swern oxidation / 3.2: Wittig reaction;

DOI:10.1016/j.tetasy.2004.12.001

Reference yield:

methyl 3-O-allyl-2-O-benzyl-β-L-arabinopyranoside (848842-31-9) → methyl 2-O-benzyl-4-deoxy-4-C-methylene-β-L-threo-pentopyranoside (848842-34-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 56 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -40 - 20 °C

2.1: n-butyllithium / diethyl ether; hexane / 1 h / 20 °C

2.2: 40 percent / diethyl ether; hexane

3.1: 61 percent / 4-toluenesulfonic acid / palladium/charcoal / methanol / Heating

With n-butyllithium; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In methanol; diethyl ether; hexane; dichloromethane; 1.1: Swern oxidation / 2.2: Wittig reaction;

DOI:10.1016/j.tetasy.2004.12.001

upstream raw materials:

methyl 3-O-allyl-2-O-benzyl-4-deoxy-4-C-methylene-β-L-threo-pentopyranoside

methyl 3-O-allyl-2-O-benzyl-β-L-threo-pent-4-ulopyranoside

methyl 3-O-allyl-2-O-benzyl-β-L-arabinopyranoside

Downstream raw materials:

(3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,3R,4S)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester