(2R,5S,6R,7R)-1-[(2S,4S,6S)-6-(3-Benzyloxy-propyl)-2-phenyl-[1,3]dioxan-4-yl]-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-octan-4-one

Base Information

• Chemical Name: (2R,5S,6R,7R)-1-[(2S,4S,6S)-6-(3-Benzyloxy-propyl)-2-phenyl-[1,3]dioxan-4-yl]-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-octan-4-one
• CAS No.: 915141-66-1
• Molecular Formula: C₅₀H₇₈O₈Si₂
• Molecular Weight: 863.336
• Mol file: 915141-66-1.mol

Synonyms:

Chemical Property of (2R,5S,6R,7R)-1-[(2S,4S,6S)-6-(3-Benzyloxy-propyl)-2-phenyl-[1,3]dioxan-4-yl]-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-octan-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S,6R,7R)-1-[(2S,4S,6S)-6-(3-Benzyloxy-propyl)-2-phenyl-[1,3]dioxan-4-yl]-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-octan-4-one

There total 10 articles about (2R,5S,6R,7R)-1-[(2S,4S,6S)-6-(3-Benzyloxy-propyl)-2-phenyl-[1,3]dioxan-4-yl]-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-octan-4-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: 98.0%

(2R,5S,6R,7R)-1-[(2S,4R,6S)-6-(3-Benzyloxy-propyl)-2-phenyl-[1,3]dioxan-4-yl]-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-5,7-dimethyl-octan-4-one (915141-54-7) + t-butyldimethylsiyl triflate (69739-34-0) → (2R,5S,6R,7R)-1-[(2S,4S,6S)-6-(3-Benzyloxy-propyl)-2-phenyl-[1,3]dioxan-4-yl]-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-octan-4-one (915141-66-1)

Guidance literature:

With triethylamine;

DOI:10.1055/s-2006-949614

Reference yield:

(S)‐7‐(benzyloxy)hept‐1‐en‐4‐ol (127793-67-3) → (2R,5S,6R,7R)-1-[(2S,4S,6S)-6-(3-Benzyloxy-propyl)-2-phenyl-[1,3]dioxan-4-yl]-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-octan-4-one (915141-66-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / second generation Grubbs' catalyst / CH₂Cl₂ / Heating

2: 74 percent / t-BuOK

3: 94 percent / DIBAL-H / -95 °C

4: 75 percent / BF₃*OEt₂

5: 98 percent / Et₃N

With boron trifluoride diethyl etherate; potassium tert-butylate; diisobutylaluminium hydride; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; 4: Mukaiyama aldol reaction;

DOI:10.1055/s-2006-949614

Reference yield:

1-(benzyloxy)-4,5-epoxypentane (112482-35-6) → (2R,5S,6R,7R)-1-[(2S,4S,6S)-6-(3-Benzyloxy-propyl)-2-phenyl-[1,3]dioxan-4-yl]-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-octan-4-one (915141-66-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 47 percent / C₃₈H₅₅O₄N₂Co / H₂O

2: 96 percent / CuI

3: 94 percent / second generation Grubbs' catalyst / CH₂Cl₂ / Heating

4: 74 percent / t-BuOK

5: 94 percent / DIBAL-H / -95 °C

6: 75 percent / BF₃*OEt₂

7: 98 percent / Et₃N

With copper(l) iodide; boron trifluoride diethyl etherate; potassium tert-butylate; diisobutylaluminium hydride; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; C₃₈H₅₅O₄N₂Co; In dichloromethane; water; 6: Mukaiyama aldol reaction;

DOI:10.1055/s-2006-949614

upstream raw materials:

(2R,5S,6R,7R)-1-[(2S,4R,6S)-6-(3-Benzyloxy-propyl)-2-phenyl-[1,3]dioxan-4-yl]-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-5,7-dimethyl-octan-4-one

t-butyldimethylsiyl triflate

(E)-(S)-8-Benzyloxy-5-hydroxy-oct-2-enoic acid methyl ester

2-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]acetaldehyde

Downstream raw materials:

(2S,5R,6R,7R)-1-[(2S,4S,6S)-6-(3-Benzyloxy-propyl)-2-phenyl-[1,3]dioxan-4-yl]-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-octan-4-ol