methyl (2R,3R)-(-)-N-benzyl-N-(1-formylvinyl)-2,3-di-O-isopropylidenetartramate

Base Information

Chemical Name:methyl (2R,3R)-(-)-N-benzyl-N-(1-formylvinyl)-2,3-di-O-isopropylidenetartramate
CAS No.:427882-50-6
Molecular Formula:C₁₈H₂₁NO₆
Molecular Weight:347.368
Hs Code.:

Synonyms:methyl (2R,3R)-(-)-N-benzyl-N-(1-formylvinyl)-2,3-di-O-isopropylidenetartramate

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Chemical Property of methyl (2R,3R)-(-)-N-benzyl-N-(1-formylvinyl)-2,3-di-O-isopropylidenetartramate

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Technology Process of methyl (2R,3R)-(-)-N-benzyl-N-(1-formylvinyl)-2,3-di-O-isopropylidenetartramate

There total 4 articles about methyl (2R,3R)-(-)-N-benzyl-N-(1-formylvinyl)-2,3-di-O-isopropylidenetartramate 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: 72.0%

: 427882-48-2
methyl (2R,3R)-(-)-N-benzyl-N-[(1R)-1-benzyloxymethyl-2-hydroxyethyl]-2,3-di-O-isopropylidenetartramate

: 427882-50-6
methyl (2R,3R)-(-)-N-benzyl-N-(1-formylvinyl)-2,3-di-O-isopropylidenetartramate

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -60 ℃; for 0.25h;
DOI:10.1002/1099-0690(200203)2002:5<873::AID-EJOC873>3.0.CO;2-V

Reference yield:

: 98-88-4
benzoyl chloride

: 427882-50-6
methyl (2R,3R)-(-)-N-benzyl-N-(1-formylvinyl)-2,3-di-O-isopropylidenetartramate

Guidance literature:: Multi-step reaction with 4 steps

1: 5 percent / Et₃N / tetrahydrofuran / 15 h / 20 °C

2: 98 percent / LiAlH₄ / tetrahydrofuran

3: 70 percent / PyBrOP; DIPEA / CH₂Cl₂

4: 72 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -60 °C

With lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In tetrahydrofuran; dichloromethane; 4: Swern oxidation;
DOI:10.1002/1099-0690(200203)2002:5<873::AID-EJOC873>3.0.CO;2-V

Reference yield:

: 170956-48-6
(2R)-(+)-2-(N-benzylamino)-3-benzyloxy-1-propanol

: 427882-50-6
methyl (2R,3R)-(-)-N-benzyl-N-(1-formylvinyl)-2,3-di-O-isopropylidenetartramate

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / PyBrOP; DIPEA / CH₂Cl₂

2: 72 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -60 °C

With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; 2: Swern oxidation;
DOI:10.1002/1099-0690(200203)2002:5<873::AID-EJOC873>3.0.CO;2-V