(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

Base Information

• Chemical Name: (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
• CAS No.: 915141-54-7
• Molecular Formula: C₄₄H₆₄O₈Si
• Molecular Weight: 749.073
• Mol file: 915141-54-7.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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: 75.0%

2-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]acetaldehyde (915141-48-9) + 1-{(1R,2S)-1-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-3-trimethylsilanyloxy-but-3-enyloxymethyl}-4-methoxy-benzene (915141-52-5) → (2S,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 + (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)

Guidance literature:

With boron trifluoride diethyl etherate;

DOI:10.1055/s-2006-949614

Reference yield:

1-(benzyloxy)-4,5-epoxypentane (112482-35-6) → (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)

Guidance literature:

Multi-step reaction with 6 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

With copper(l) iodide; boron trifluoride diethyl etherate; potassium tert-butylate; diisobutylaluminium hydride; 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

Reference yield:

(S)‐7‐(benzyloxy)hept‐1‐en‐4‐ol (127793-67-3) → (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)

Guidance literature:

Multi-step reaction with 4 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

With boron trifluoride diethyl etherate; potassium tert-butylate; diisobutylaluminium hydride; 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

upstream raw materials:

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

1-{(1R,2S)-1-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-3-trimethylsilanyloxy-but-3-enyloxymethyl}-4-methoxy-benzene

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

(3S,4R,5R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-2-one

Downstream raw materials:

(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

(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