N-benzyl-N'-[(1S)-1-formyl-1-methyl]-(2R,3R)-2,3-di-O-isopropylidenetartramic acid methyl ester

Base Information

• Chemical Name: N-benzyl-N'-[(1S)-1-formyl-1-methyl]-(2R,3R)-2,3-di-O-isopropylidenetartramic acid methyl ester
• CAS No.: 250137-75-8
• Molecular Formula: C₁₈H₂₃NO₆
• Molecular Weight: 349.384
• Mol file: 250137-75-8.mol

Synonyms:N-benzyl-N'-[(1S)-1-formyl-1-methyl]-(2R,3R)-2,3-di-O-isopropylidenetartramic acid methyl ester

Chemical Property of N-benzyl-N'-[(1S)-1-formyl-1-methyl]-(2R,3R)-2,3-di-O-isopropylidenetartramic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyl-N'-[(1S)-1-formyl-1-methyl]-(2R,3R)-2,3-di-O-isopropylidenetartramic acid methyl ester

There total 3 articles about N-benzyl-N'-[(1S)-1-formyl-1-methyl]-(2R,3R)-2,3-di-O-isopropylidenetartramic acid methyl ester 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: 90.0%

N-benzyl-N'-[(1S)-2-hydroxy-1-methylethyl]-(2R,3R)-2,3-di-isopropylidenetartramic acid methyl ester (250137-68-9) → N-benzyl-N'-[(1S)-1-formyl-1-methyl]-(2R,3R)-2,3-di-O-isopropylidenetartramic acid methyl ester (250137-75-8)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -60 ℃; for 0.25h;

DOI:10.1021/jo9904967

Reference yield:

(S)-N-benzylalaninol (6940-80-3,6940-81-4) → N-benzyl-N'-[(1S)-1-formyl-1-methyl]-(2R,3R)-2,3-di-O-isopropylidenetartramic acid methyl ester (250137-75-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / bromotripyrrolidinophosphonium hexafluorophosphate; DIPEA / CH₂Cl₂ / 12 h / 25 °C

2: 90 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; 1: Acylation / 2: Oxidation;

DOI:10.1021/jo9904967

Reference yield:

(4R,5R)-5-(methoxycarbonyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid (67812-33-3) → N-benzyl-N'-[(1S)-1-formyl-1-methyl]-(2R,3R)-2,3-di-O-isopropylidenetartramic acid methyl ester (250137-75-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / bromotripyrrolidinophosphonium hexafluorophosphate; DIPEA / CH₂Cl₂ / 12 h / 25 °C

2: 90 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; 1: Acylation / 2: Oxidation;

DOI:10.1021/jo9904967

upstream raw materials:

N-benzyl-N'-[(1S)-2-hydroxy-1-methylethyl]-(2R,3R)-2,3-di-isopropylidenetartramic acid methyl ester

(S)-N-benzylalaninol

(4R,5R)-5-(methoxycarbonyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid

Downstream raw materials:

methyl (1R,4S,5S,7R)-3-benzyl-2-oxo-4-exo-methyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate