methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate

Base Information

• Chemical Name: methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate
• CAS No.: 121357-96-8
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321
• Mol file: 121357-96-8.mol

Synonyms:methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate

Chemical Property of methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate

There total 9 articles about methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate 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: 98.0%

benzyl bromide (100-39-0) + methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate (92973-40-5) → methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate (121357-96-8)

Guidance literature:

With silver(l) oxide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tet.2012.12.076

Reference yield: 80.0%

methanol (67-56-1) + 2-O-benzyl-3,4-O-isopropylidene-L-threose (100906-42-1) → methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate (121357-96-8)

Guidance literature:

With bromine; sodium hydrogencarbonate; In water; at 20 ℃; for 2h;

DOI:10.1080/00397911.2012.714041

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threitol (84379-53-3) → methyl (2R,3S)-2-benzyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate (121357-96-8)

Guidance literature:

Multi-step reaction with 2 steps

1: DMSO, oxalyl chloride / CH₂Cl₂ / 0.25 h / -60 °C

2: NaHCO₃, bromine / H₂O / 2 h / Ambient temperature

With oxalyl dichloride; bromine; sodium hydrogencarbonate; dimethyl sulfoxide; In dichloromethane; water;

DOI:10.1055/s-1988-27708

upstream raw materials:

methanol

2-O-benzyl-3,4-O-isopropylidene-L-threose

(2R,3R)-2-benzyloxy-3-hydroxy-1,4-butanedioic acid dimethyl ester

2,2-dimethoxy-propane

Downstream raw materials:

2-O-benzyl-3,4-O-isopropylidene-L-threitol

Methanesulfonic acid (S)-2-benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

(2S)-3-azido-2-benzyloxypropanal

(2S,3S)-4-azido-3-benzyloxy-1,2-O-isopropylidene-1,2-butanediol