(2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3,4-di-hydroxy-pentane

Base Information

• Chemical Name: (2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3,4-di-hydroxy-pentane
• CAS No.: 136985-04-1
• Molecular Formula: C₁₃H₂₈O₂S₂
• Molecular Weight: 280.496
• Mol file: 136985-04-1.mol

Synonyms:(2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3,4-di-hydroxy-pentane

Chemical Property of (2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3,4-di-hydroxy-pentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3,4-di-hydroxy-pentane

There total 1 articles about (2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3,4-di-hydroxy-pentane 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%

(2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3-hydroxy-5-(methanesulfonyloxy)-4-(tert-butyldiphenylsiloxy)-pentane (136985-03-0) → tert-butyldiphenylsilane (33729-92-9) + (2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3,4-di-hydroxy-pentane (136985-04-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; 1.) -70 deg C, 10 min, 2.) without cooling, 1 h, 3.) 50 deg C, 3 h;

DOI:10.1016/S0040-4020(01)86575-3

Reference yield: 97.0%

N-benzyloxycarbonyl-O-t-butyl-L-threonine (16966-09-9) + (2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3,4-di-hydroxy-pentane (136985-04-1) → (2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-hydroxy-pentane (136985-05-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; 1.) 0 deg C, 15 min, 2.) room temperature, 6 h;

DOI:10.1016/S0040-4020(01)86575-3

Reference yield:

(2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3,4-di-hydroxy-pentane (136985-04-1) → (2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-3-isovaleryloxy-pentanoic acid (69918-30-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / DCC, DMAP / CH₂Cl₂ / 1.) 0 deg C, 15 min, 2.) room temperature, 6 h

2: 78 percent / pyridine / 23 h / 40 °C

3: CdCO₃, HgCl₂ / acetonitrile; H₂O / 5.33 h

4: CrO₃ / pyridine; acetic acid / 22 h / Ambient temperature

With pyridine; chromium(VI) oxide; dmap; cadmium(II) carbonate; dicyclohexyl-carbodiimide; mercury dichloride; In pyridine; dichloromethane; water; acetic acid; acetonitrile;

DOI:10.1016/S0040-4020(01)86575-3

upstream raw materials:

(2R, 3R, 4S) 2-butyl-1,1-bis(ethylthio)-3-hydroxy-5-(methanesulfonyloxy)-4-(tert-butyldiphenylsiloxy)-pentane

Downstream raw materials:

(2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-hydroxy-pentane

(2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-3-isovaleryloxy-pentanoic acid

(2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-isovaleryloxy-pentane