methyl (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-4-phenoxythiocarbonyloxycyclohex-1-enecarboxylate

Base Information

• Chemical Name: methyl (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-4-phenoxythiocarbonyloxycyclohex-1-enecarboxylate
• CAS No.: 101906-40-5
• Molecular Formula: C₂₇H₄₄O₆SSi₂
• Molecular Weight: 552.88
• Mol file: 101906-40-5.mol

Synonyms:methyl (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-4-phenoxythiocarbonyloxycyclohex-1-enecarboxylate

Chemical Property of methyl (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-4-phenoxythiocarbonyloxycyclohex-1-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-4-phenoxythiocarbonyloxycyclohex-1-enecarboxylate

There total 5 articles about methyl (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-4-phenoxythiocarbonyloxycyclohex-1-enecarboxylate 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: 93.0%

Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate (101906-39-2) + phenylcarbonochloridothioate (1005-56-7) → methyl (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-4-phenoxythiocarbonyloxycyclohex-1-enecarboxylate (101906-40-5)

Guidance literature:

With dmap; In acetonitrile; for 20h; Ambient temperature;

DOI:10.1016/S0040-4039(00)79117-9

Reference yield:

methyl shikimate (40983-58-2) → methyl (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-4-phenoxythiocarbonyloxycyclohex-1-enecarboxylate (101906-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / Et₃N, DMAP, Bu₄NI / dimethylformamide / 1.) 0 deg C, 1 h, 2.) r.t., 3 h

2: 82 percent / DMAP / acetonitrile / 24 h / Ambient temperature

With dmap; tetra-(n-butyl)ammonium iodide; triethylamine; In N,N-dimethyl-formamide; acetonitrile;

Reference yield:

shikimic acid (138-59-0) → methyl (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-4-phenoxythiocarbonyloxycyclohex-1-enecarboxylate (101906-40-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / HCl / 4 h / 60 °C

2: 82 percent / Et₃N, DMAP / dimethylformamide / 6 h / 0 °C

3: 93 percent / DMAP / acetonitrile / 20 h / Ambient temperature

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

DOI:10.1016/S0040-4039(00)79117-9

upstream raw materials:

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

phenylcarbonochloridothioate

methyl shikimate

tert-butyldimethylsilyl chloride

Downstream raw materials:

(3aR,4R,5S,6R,7aR)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-5-phenoxythiocarbonyloxy-3,3a,4,5,6,7-hexahydro-indazole-7a-carboxylic acid methyl ester

(3aS,4R,5S,6R,7aS)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-5-phenoxythiocarbonyloxy-3,3a,4,5,6,7-hexahydro-indazole-7a-carboxylic acid methyl ester

(3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-1-hydroxymethyl-4-phenoxythiocarbonyloxycyclohex-1-ene

(3S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-1-hydroxymethylcyclohex-1-ene