(4R,6R)-4-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-[1,3]dioxane

Base Information

• Chemical Name: (4R,6R)-4-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-[1,3]dioxane
• CAS No.: 332179-91-6
• Molecular Formula: C₃₈H₇₀O₆Si₂
• Molecular Weight: 679.141
• Mol file: 332179-91-6.mol

Synonyms:(4R,6R)-4-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-[1,3]dioxane

Chemical Property of (4R,6R)-4-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-[1,3]dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,6R)-4-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-[1,3]dioxane

There total 15 articles about (4R,6R)-4-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-[1,3]dioxane 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: 87.0%

2,2-dimethoxy-propane (77-76-9) + (E)-(3S,5S,7R,10S,11S)-1,11-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-10,12-dimethyl-tridec-8-ene-5,7-diol (332179-89-2) → (4R,6R)-4-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-[1,3]dioxane (332179-91-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; for 16h;

DOI:10.1016/S0040-4039(00)02205-X

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (4R,6R)-4-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-[1,3]dioxane (332179-91-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2: LiAlH₄ / 3 h / -78 - 0 °C

3: H₂ / Pd(OH)2/C / ethyl acetate / 1 h

4: NaIO₄ / methanol; H₂O / 0.67 h

5: acetonitrile / 20 h / 84 °C

6: DIBAL / diethyl ether / 1.5 h / -78 - 20 °C

7: Dess-Martin periodinane / CH₂Cl₂

9: 87 percent / PPTS / CH₂Cl₂ / 16 h

With 2,6-dimethylpyridine; sodium periodate; lithium aluminium tetrahydride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(00)02205-X

Reference yield:

(2S,4R,5S)-2-benzyloxy-5-hydroxy-4,6-dimethyl-3-heptanone (164145-48-6) → (4R,6R)-4-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-[1,3]dioxane (332179-91-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2: LiAlH₄ / 3 h / -78 - 0 °C

3: H₂ / Pd(OH)2/C / ethyl acetate / 1 h

4: NaIO₄ / methanol; H₂O / 0.67 h

5: acetonitrile / 20 h / 84 °C

6: DIBAL / diethyl ether / 1.5 h / -78 - 20 °C

7: Dess-Martin periodinane / CH₂Cl₂

9: 87 percent / PPTS / CH₂Cl₂ / 16 h

With 2,6-dimethylpyridine; sodium periodate; lithium aluminium tetrahydride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(00)02205-X

upstream raw materials:

2,2-dimethoxy-propane

(E)-(3S,5S,7R,10S,11S)-1,11-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-10,12-dimethyl-tridec-8-ene-5,7-diol

t-butyldimethylsiyl triflate

p-methoxybenzyl trichloroacetate

Downstream raw materials:

(R)-4-{(4R,6R)-6-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-(4-methoxy-benzyloxy)-butyraldehyde