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

Base Information

• Chemical Name: (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-1-hydroxymethyl-4-phenoxythiocarbonyloxycyclohex-1-ene
• CAS No.: 144699-09-2
• Molecular Formula: C₂₆H₄₄O₅SSi₂
• Molecular Weight: 524.869
• Mol file: 144699-09-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-1-hydroxymethyl-4-phenoxythiocarbonyloxycyclohex-1-ene 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 (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-4-phenoxythiocarbonyloxycyclohex-1-enecarboxylate (101906-40-5) → (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-1-hydroxymethyl-4-phenoxythiocarbonyloxycyclohex-1-ene (144699-09-2)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.25h;

Reference yield:

methyl shikimate (40983-58-2) → (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-1-hydroxymethyl-4-phenoxythiocarbonyloxycyclohex-1-ene (144699-09-2)

Guidance literature:

Multi-step reaction with 3 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

3: 93 percent / DIBAL-H / toluene / 0.25 h / -78 °C

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

Reference yield:

Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate (101906-39-2) → (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-1-hydroxymethyl-4-phenoxythiocarbonyloxycyclohex-1-ene (144699-09-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / DMAP / acetonitrile / 24 h / Ambient temperature

2: 93 percent / DIBAL-H / toluene / 0.25 h / -78 °C

With dmap; diisobutylaluminium hydride; In toluene; acetonitrile;

upstream raw materials:

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

methyl shikimate

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

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

(3S,5S)-3,5-bis(tert-butyldimethylsilyloxy)cyclohex-1-enecarbaldehyde

4-deoxy-3-dehydroshikimic acid

4-deoxyshikimic acid