(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

Base Information

• Chemical Name: (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
• CAS No.: 332179-79-0
• Molecular Formula: C₃₂H₅₄O₆Si
• Molecular Weight: 562.863

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 16 articles about (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 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:

(S)-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)-butan-1-ol → (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 (332179-79-0)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃; for 1.5h;

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

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (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 (332179-79-0)

Guidance literature:

Multi-step reaction with 11 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

10: TBAF / tetrahydrofuran / 1.5 h

11: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

With 2,6-dimethylpyridine; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile; 11: Swern oxidation;

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) → (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 (332179-79-0)

Guidance literature:

Multi-step reaction with 11 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

10: TBAF / tetrahydrofuran / 1.5 h

11: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

With 2,6-dimethylpyridine; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile; 11: Swern oxidation;

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

upstream raw materials:

t-butyldimethylsiyl triflate

p-methoxybenzyl trichloroacetate

(3R)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-ol

(E)-(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-enoic acid methyl ester

Downstream raw materials:

(E)-(2S,4S,8S,10R,11S)-1-{(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}-4-hydroxy-13-iodo-2,8-bis-(4-methoxy-benzyloxy)-11-methyl-10-triisopropylsilanyloxy-tridec-12-en-6-one

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