4,6-bis-tert-butyldimethylsilanyloxy-2-methoxycarbonylmethyl-3-methylbenzoic acid methyl ester

Base Information

• Chemical Name: 4,6-bis-tert-butyldimethylsilanyloxy-2-methoxycarbonylmethyl-3-methylbenzoic acid methyl ester
• CAS No.: 869964-34-1
• Molecular Formula: C₂₄H₄₂O₆Si₂
• Molecular Weight: 482.765
• Mol file: 869964-34-1.mol

Synonyms:4,6-bis-tert-butyldimethylsilanyloxy-2-methoxycarbonylmethyl-3-methylbenzoic acid methyl ester

Chemical Property of 4,6-bis-tert-butyldimethylsilanyloxy-2-methoxycarbonylmethyl-3-methylbenzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-bis-tert-butyldimethylsilanyloxy-2-methoxycarbonylmethyl-3-methylbenzoic acid methyl ester

There total 1 articles about 4,6-bis-tert-butyldimethylsilanyloxy-2-methoxycarbonylmethyl-3-methylbenzoic 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: 99.0%

t-butyldimethylsiyl triflate (69739-34-0) + 4,6-dihydroxy-2-methoxycarbonylmethyl-3-methylbenzoic acid methyl ester (292157-65-4) → 4,6-bis-tert-butyldimethylsilanyloxy-2-methoxycarbonylmethyl-3-methylbenzoic acid methyl ester (869964-34-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1021/ol0520267

Reference yield: 93.0%

4,6-bis-tert-butyldimethylsilanyloxy-2-methoxycarbonylmethyl-3-methylbenzoic acid methyl ester (869964-34-1) → 4,6-bis-tert-butyldimethylsilanyloxy-3-methyl-2-(2-oxoethyl)benzoic acid methyl ester (869964-21-6)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; Inert atmosphere;

DOI:10.1021/ja207331m

Reference yield:

4,6-bis-tert-butyldimethylsilanyloxy-2-methoxycarbonylmethyl-3-methylbenzoic acid methyl ester (869964-34-1) → (2R,3R)-4,6-bis-tert-butyldimethylsilanyloxy-2-hydroxy-3-methylpent-4-enyl-3-methylbenzoic acid methyl ester (869964-22-7)

Guidance literature:

Multi-step reaction with 2 steps

1: di-iso-butylaluminum hydride / CH₂Cl₂; hexane / 2 h / -78 °C

2: diethyl ether; tetrahydrofuran; hexane / 2.5 h / -78 °C

With diisobutylaluminum hydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 2: Brown crotylation;

DOI:10.1021/ol0520267

upstream raw materials:

t-butyldimethylsiyl triflate

4,6-dihydroxy-2-methoxycarbonylmethyl-3-methylbenzoic acid methyl ester

Downstream raw materials:

4,6-bis-tert-butyldimethylsilanyloxy-3-methyl-2-(2-oxoethyl)benzoic acid methyl ester

(2R,3R)-4,6-bis-tert-butyldimethylsilanyloxy-2-hydroxy-3-methylpent-4-enyl-3-methylbenzoic acid methyl ester

(2R,3R)-4,6-bis-tert-butyldimethylsilanyloxy-2-(2-tert-butyldimethylsilanyloxy-3-methyl-4-oxobutyl)-3-methylbenzoic acid methyl ester

(2R,3R)-4,6-bis-tert-butyldimethylsilanyloxy-2-(2-tert-butyldimethylsilanyloxy-3-methylpent-4-enyl)-3-methylbenzoic acid methyl ester