(3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-pentane-1,4-diol

Base Information

• Chemical Name: (3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-pentane-1,4-diol
• CAS No.: 208840-42-0
• Molecular Formula: C₂₉H₃₈O₅Si
• Molecular Weight: 494.703
• Mol file: 208840-42-0.mol

Synonyms:(3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-pentane-1,4-diol

Chemical Property of (3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-pentane-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-pentane-1,4-diol

There total 1 articles about (3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-pentane-1,4-diol 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: 91.0%

(2R,3S)-5-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-pentan-2-ol (199472-28-1) → (3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-pentane-1,4-diol (208840-42-0)

Guidance literature:

With hydrogen; Ra-Ni(W₂); In ethanol; at 20 ℃; for 24h;

DOI:10.1246/cl.1998.409

Reference yield: 65.0%

(3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-pentane-1,4-diol (208840-42-0) → (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-ol

Guidance literature:

With dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1246/cl.1998.409

Reference yield:

(3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-pentane-1,4-diol (208840-42-0) → 2-[(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-propan-2-ol

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / IBX, DMSO / tetrahydrofuran / 2 h / 20 °C

2: 73 percent / DMAP, Et₃N / CH₂Cl₂ / 30 h / 0 °C

3: 23 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -78 °C

4: 64 percent / lithium 4,4'-di-tert-butylbiphenylide / tetrahydrofuran / 0.17 h / -78 °C

With dmap; 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane;

DOI:10.1246/cl.1998.409

upstream raw materials:

(2R,3S)-5-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-pentan-2-ol

Downstream raw materials:

tert-Butyl-[(2R,3S,5R)-3-(4-methoxy-benzyloxy)-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy]-diphenyl-silane

tert-Butyl-[(2R,3S,5S)-3-(4-methoxy-benzyloxy)-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy]-diphenyl-silane