methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside

Base Information

Chemical Name:methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside
CAS No.:50711-27-8
Molecular Formula:C₂₀H₂₂O₄
Molecular Weight:326.392
Hs Code.:

Synonyms:methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside

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Chemical Property of methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside

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Technology Process of methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside

There total 5 articles about methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside 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: 70.0%

: 17791-36-5
methyl 2,3-di-O-benzyl-α-D-glucopyranoside

: 50711-27-8
methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside

Guidance literature:: methyl 2,3-di-O-benzyl-α-D-glucopyranoside; With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; tetrabutylammomium bromide; potassium bromide; In dichloromethane; water; at 0 ℃; for 0.75h;

With N,N-dimethylformamide dineopentyl acetal; In toluene; at 120 ℃; for 1h; Further stages.;
DOI:10.1021/ol026175q

Reference yield:

: 444600-30-0
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(dimethyl-phenyl-silanyl)-methyl]-6-methoxy-tetrahydro-pyran-3-ol

: 50711-27-8
methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: peracetic acid; potassium bromide; sodium acetate / acetic acid / 20 h / 0 - 20 °C

2.1: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; sodium hypochlorite; sodium hydrogen carbonate / tetra-n-butylammonium bromide; potassium bromide / CH₂Cl₂; H₂O / 0.75 h / 0 °C

2.2: 70 percent / N,N-dimethylformamide dineopentyl acetal / toluene / 1 h / 120 °C

With peracetic acid; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium acetate; sodium hydrogencarbonate; potassium bromide; tetrabutylammomium bromide; potassium bromide; In dichloromethane; water; acetic acid; 1.1: Tamao-Fleming oxidation;
DOI:10.1021/ol026175q

Reference yield:

: (3S,4R,5R)-4,5-Bis-benzyloxy-3-methoxy-2,7-dioxa-bicyclo[4.1.0]heptane

: 50711-27-8
methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: copper(I) iodide / tetrahydrofuran / 0.33 h / -10 °C

2.1: peracetic acid; potassium bromide; sodium acetate / acetic acid / 20 h / 0 - 20 °C

3.1: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; sodium hypochlorite; sodium hydrogen carbonate / tetra-n-butylammonium bromide; potassium bromide / CH₂Cl₂; H₂O / 0.75 h / 0 °C

3.2: 70 percent / N,N-dimethylformamide dineopentyl acetal / toluene / 1 h / 120 °C

With peracetic acid; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; copper(l) iodide; sodium acetate; sodium hydrogencarbonate; potassium bromide; tetrabutylammomium bromide; potassium bromide; In tetrahydrofuran; dichloromethane; water; acetic acid; 1.1: Grignard addition / 2.1: Tamao-Fleming oxidation;
DOI:10.1021/ol026175q