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

Base Information

Chemical Name:methyl 3-O-allyl-2-O-benzyl-4-deoxy-4-C-methylene-β-D-threo-pentopyranoside
CAS No.:848842-29-5
Molecular Formula:C₁₇H₂₂O₄
Molecular Weight:290.359
Hs Code.:

Synonyms:methyl 3-O-allyl-2-O-benzyl-4-deoxy-4-C-methylene-β-D-threo-pentopyranoside

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Chemical Property of methyl 3-O-allyl-2-O-benzyl-4-deoxy-4-C-methylene-β-D-threo-pentopyranoside

Chemical Property:

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Technology Process of methyl 3-O-allyl-2-O-benzyl-4-deoxy-4-C-methylene-β-D-threo-pentopyranoside

There total 3 articles about methyl 3-O-allyl-2-O-benzyl-4-deoxy-4-C-methylene-β-D-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: 50.0%

: 848842-28-4
methyl 3-O-allyl-2-O-benzyl-β-D-threo-pent-4-ulopyranoside

: 1779-49-3
Methyltriphenylphosphonium bromide

: 848842-29-5
methyl 3-O-allyl-2-O-benzyl-4-deoxy-4-C-methylene-β-D-threo-pentopyranoside

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In diethyl ether; hexane; at 20 ℃; for 1h;

methyl 3-O-allyl-2-O-benzyl-β-D-threo-pent-4-ulopyranoside; In diethyl ether; hexane; for 1h;
DOI:10.1016/j.tetasy.2004.12.001

Reference yield:

: 848842-27-3
methyl 3-O-allyl-2-O-benzyl-β-D-arabinopyranoside

: 848842-29-5
methyl 3-O-allyl-2-O-benzyl-4-deoxy-4-C-methylene-β-D-threo-pentopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 68 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 6.5 h / -40 - 20 °C

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

2.2: 50 percent / diethyl ether; hexane / 1 h

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In diethyl ether; hexane; dichloromethane; 1.1: Swern oxidation / 2.2: Wittig reaction;
DOI:10.1016/j.tetasy.2004.12.001

Reference yield:

: 149454-88-6
methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside

: 848842-29-5
methyl 3-O-allyl-2-O-benzyl-4-deoxy-4-C-methylene-β-D-threo-pentopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: acetic acid; water / 20 °C

1.2: dibutyltin oxide / toluene / Heating

1.3: 73 percent / caesium fluoride / dimethylformamide / 20 °C

2.1: 68 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 6.5 h / -40 - 20 °C

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

3.2: 50 percent / diethyl ether; hexane / 1 h

With n-butyllithium; oxalyl dichloride; water; acetic acid; dimethyl sulfoxide; triethylamine; In diethyl ether; hexane; dichloromethane; 2.1: Swern oxidation / 3.2: Wittig reaction;
DOI:10.1016/j.tetasy.2004.12.001