(3S,4S,5S,9S,10S,11S)-1,13-bis(benzyloxy)-5,9-dimethyl-3,4,10,11-tetrahydroxytridecane-7-one

Base Information

• Chemical Name: (3S,4S,5S,9S,10S,11S)-1,13-bis(benzyloxy)-5,9-dimethyl-3,4,10,11-tetrahydroxytridecane-7-one
• CAS No.: 440643-05-0
• Molecular Formula: C₂₉H₄₂O₇
• Molecular Weight: 502.648
• Mol file: 440643-05-0.mol

Synonyms:(3S,4S,5S,9S,10S,11S)-1,13-bis(benzyloxy)-5,9-dimethyl-3,4,10,11-tetrahydroxytridecane-7-one

Chemical Property of (3S,4S,5S,9S,10S,11S)-1,13-bis(benzyloxy)-5,9-dimethyl-3,4,10,11-tetrahydroxytridecane-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5S,9S,10S,11S)-1,13-bis(benzyloxy)-5,9-dimethyl-3,4,10,11-tetrahydroxytridecane-7-one

There total 6 articles about (3S,4S,5S,9S,10S,11S)-1,13-bis(benzyloxy)-5,9-dimethyl-3,4,10,11-tetrahydroxytridecane-7-one 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:

(3E,5S,9S,10E)-5,9-dimethyl-1,13-bis(benzyloxy)-3,10-tridecadien-7-one (214483-93-9) → (3S,4S,5S,9S,10S,11S)-1,13-bis(benzyloxy)-5,9-dimethyl-3,4,10,11-tetrahydroxytridecane-7-one (440643-05-0)

Guidance literature:

With Sharpless's AD-mix-α; In water; tert-butyl alcohol; at 0 ℃;

DOI:10.1021/jo981181e

Reference yield:

(S,E)-1-(benzyloxy)hex-4-en-3-ol (214483-91-7) → (3S,4S,5S,9S,10S,11S)-1,13-bis(benzyloxy)-5,9-dimethyl-3,4,10,11-tetrahydroxytridecane-7-one (440643-05-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / propionic acid / 26 h / 145 °C

2: 84 percent / HMDS; TMEDA; n-BuLi / tetrahydrofuran / 0 °C

3: 96 percent / aq. LiCl / dimethylsulfoxide / 0.67 h / 190 °C

4: AD-mix-α / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

With AD-mix-α; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; propionic acid; 1,1,1,3,3,3-hexamethyl-disilazane; lithium chloride; In tetrahydrofuran; water; dimethyl sulfoxide; tert-butyl alcohol;

DOI:10.1016/S0040-4020(02)00050-9

Reference yield:

(3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl ester (214483-92-8) → (3S,4S,5S,9S,10S,11S)-1,13-bis(benzyloxy)-5,9-dimethyl-3,4,10,11-tetrahydroxytridecane-7-one (440643-05-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / HMDS; TMEDA; n-BuLi / tetrahydrofuran / 0 °C

2: 96 percent / aq. LiCl / dimethylsulfoxide / 0.67 h / 190 °C

3: AD-mix-α / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

With AD-mix-α; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium chloride; In tetrahydrofuran; water; dimethyl sulfoxide; tert-butyl alcohol;

DOI:10.1016/S0040-4020(02)00050-9

upstream raw materials:

(3E,5S,9S,10E)-5,9-dimethyl-1,13-bis(benzyloxy)-3,10-tridecadien-7-one

(S,E)-1-(benzyloxy)hex-4-en-3-ol

(3S)-1-benzyloxy-4-hexyn-3-ol

(3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl ester

Downstream raw materials:

C₃₅H₄₈O₈Si

C₃₅H₄₈O₈Si

C₃₈H₅₂O₈Si

C₅₃H₈₈O₈Si₃