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

Base Information

Chemical Name:methyl 3-O-allyl-2-O-benzyl-β-D-threo-pent-4-ulopyranoside
CAS No.:848842-28-4
Molecular Formula:C₁₆H₂₀O₅
Molecular Weight:292.332
Hs Code.:

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

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Chemical Property of methyl 3-O-allyl-2-O-benzyl-β-D-threo-pent-4-ulopyranoside

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Technology Process of methyl 3-O-allyl-2-O-benzyl-β-D-threo-pent-4-ulopyranoside

There total 2 articles about methyl 3-O-allyl-2-O-benzyl-β-D-threo-pent-4-ulopyranoside 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: 68.0%

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

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

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -40 - 20 ℃; for 6.5h;
DOI:10.1016/j.tetasy.2004.12.001

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

With oxalyl dichloride; water; acetic acid; dimethyl sulfoxide; triethylamine; In dichloromethane; 2.1: Swern oxidation;
DOI:10.1016/j.tetasy.2004.12.001

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