(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-phenoxythiocarbonyloxy-cyclohex-1-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-phenoxythiocarbonyloxy-cyclohex-1-enecarboxylic acid methyl ester
• CAS No.: 101906-42-7
• Molecular Formula: C₂₈H₄₆O₆SSi₂
• Molecular Weight: 566.907
• Mol file: 101906-42-7.mol

Synonyms:(3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-phenoxythiocarbonyloxy-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property of (3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-phenoxythiocarbonyloxy-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-phenoxythiocarbonyloxy-cyclohex-1-enecarboxylic acid methyl ester

There total 3 articles about (3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-phenoxythiocarbonyloxy-cyclohex-1-enecarboxylic 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:

methyl shikimate (40983-58-2) → (3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-phenoxythiocarbonyloxy-cyclohex-1-enecarboxylic acid methyl ester (101906-42-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / Et₃N, DMAP / dimethylformamide / 4 h / 0 °C

2: 75 percent / DMAP / acetonitrile / 6 h / 20 °C

3: 1.) Et₂O, 20 deg C, 12h, 2.) 125 deg C, DMSO, 4h

With dmap; triethylamine; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(00)94991-8

Reference yield:

Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate (101906-39-2) → (3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-phenoxythiocarbonyloxy-cyclohex-1-enecarboxylic acid methyl ester (101906-42-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / DMAP / acetonitrile / 6 h / 20 °C

2: 1.) Et₂O, 20 deg C, 12h, 2.) 125 deg C, DMSO, 4h

With dmap; In acetonitrile;

DOI:10.1016/S0040-4039(00)94991-8

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (3R,4S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-phenoxythiocarbonyloxy-cyclohex-1-enecarboxylic acid methyl ester (101906-42-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / Et₃N, DMAP / dimethylformamide / 4 h / 0 °C

2: 75 percent / DMAP / acetonitrile / 6 h / 20 °C

3: 1.) Et₂O, 20 deg C, 12h, 2.) 125 deg C, DMSO, 4h

With dmap; triethylamine; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(00)94991-8

upstream raw materials:

methyl shikimate

Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate

tert-butyldimethylsilyl chloride

Downstream raw materials:

(1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether

(3S,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-2-methylcyclohex-1-en-1-carboxaldehyde

methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate

Thiocarbonic acid O-[(1S,2R,6R)-2,6-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxymethyl-3-methyl-cyclohex-3-enyl] ester O-phenyl ester