methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate

Base Information

• Chemical Name: methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate
• CAS No.: 901129-88-2
• Molecular Formula: C₂₁H₄₄O₈SSi₂
• Molecular Weight: 512.813
• Mol file: 901129-88-2.mol

Synonyms:methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate

Chemical Property of methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate

There total 3 articles about methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate 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: 95.0%

methyl quinicate (135711-62-5) + methanesulfonyl chloride (124-63-0) → methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate (901129-88-2)

Guidance literature:

With pyridine; at 0 - 20 ℃;

DOI:10.1021/acs.jafc.6b02472

Reference yield:

D-(-)-quinic acid (77-95-2) → methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate (901129-88-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / HCl / 6 h / 60 °C

2: 75 percent / Et₃N / dimethylformamide / 18 h / 0 - 20 °C

3: 80 percent / pyridine / 8 h / 20 °C

With pyridine; hydrogenchloride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jo0606249

Reference yield:

methyl (-)-quinate (191916-39-9) → methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate (901129-88-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / Et₃N / dimethylformamide / 18 h / 0 - 20 °C

2: 80 percent / pyridine / 8 h / 20 °C

With pyridine; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jo0606249

upstream raw materials:

methyl quinicate

methanesulfonyl chloride

D-(-)-quinic acid

methyl (-)-quinate

Downstream raw materials:

methyl 4-O-methanesulfonylquinate

cis-quinic acid

meso-methyl 5-epi-quinate

D-(-)-quinic acid