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

Base Information

• Chemical Name: (2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-isovaleryloxy-pentane
• CAS No.: 136985-06-3
• Molecular Formula: C₃₄H₅₇NO₇S₂
• Molecular Weight: 655.961
• Mol file: 136985-06-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-isovaleryloxy-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: 78.0%

(2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-hydroxy-pentane (136985-05-2) + isopentanoyl chloride (108-12-3) → (2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-isovaleryloxy-pentane (136985-06-3)

Guidance literature:

With pyridine; at 40 ℃; for 23h;

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

Reference yield:

benzyl 2,3-anhydro-α-L-ribopyranoside (136984-98-0) → (2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-isovaleryloxy-pentane (136985-06-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / imidazole / dimethylformamide / 0.67 h / 35 °C

2: 1.) BuLi, Me₃Al / 1.) hexane, 0 deg C, 10 min, 2.) hexane, 60 deg C, 1 h 45 min

3: 90 percent / H₂ / (Ph₃P)3RhCl / benzene; ethanol / 16 h / 760 Torr / Ambient temperature

4: 85 percent / ZnCl₂ / 1.) -10 deg C, 30 min, 2.) 0 deg C, 20 min

5: 94 percent / pyridine / 1.) 0 deg C, 15 min, 2.) room temperature, 70 min

6: 77 percent / LiAlH₄ / tetrahydrofuran / 1.) -70 deg C, 10 min, 2.) without cooling, 1 h, 3.) 50 deg C, 3 h

7: 97 percent / DCC, DMAP / CH₂Cl₂ / 1.) 0 deg C, 15 min, 2.) room temperature, 6 h

8: 78 percent / pyridine / 23 h / 40 °C

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; n-butyllithium; hydrogen; trimethylaluminum; dicyclohexyl-carbodiimide; zinc(II) chloride; Wilkinson's catalyst; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

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

Reference yield:

benzyl 2,3-anhydro-4-O-(tert-butyldiphenylsilyl)-α-L-ribopyranoside (136984-99-1) → (2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-isovaleryloxy-pentane (136985-06-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) BuLi, Me₃Al / 1.) hexane, 0 deg C, 10 min, 2.) hexane, 60 deg C, 1 h 45 min

2: 90 percent / H₂ / (Ph₃P)3RhCl / benzene; ethanol / 16 h / 760 Torr / Ambient temperature

3: 85 percent / ZnCl₂ / 1.) -10 deg C, 30 min, 2.) 0 deg C, 20 min

4: 94 percent / pyridine / 1.) 0 deg C, 15 min, 2.) room temperature, 70 min

5: 77 percent / LiAlH₄ / tetrahydrofuran / 1.) -70 deg C, 10 min, 2.) without cooling, 1 h, 3.) 50 deg C, 3 h

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

7: 78 percent / pyridine / 23 h / 40 °C

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; hydrogen; trimethylaluminum; dicyclohexyl-carbodiimide; zinc(II) chloride; Wilkinson's catalyst; In tetrahydrofuran; ethanol; dichloromethane; benzene;

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

upstream raw materials:

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

isopentanoyl chloride

benzyl 2,3-anhydro-α-L-ribopyranoside

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

Downstream raw materials:

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