2,2-Dimethyl-propionic acid (2R,3R,4S,5S)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-methyl-oct-7-enyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3R,4S,5S)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-methyl-oct-7-enyl ester
• CAS No.: 334968-82-0
• Molecular Formula: C₂₇H₄₆O₅Si
• Molecular Weight: 478.745
• Mol file: 334968-82-0.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3R,4S,5S)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-methyl-oct-7-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,3R,4S,5S)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-methyl-oct-7-enyl ester

There total 6 articles about 2,2-Dimethyl-propionic acid (2R,3R,4S,5S)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-methyl-oct-7-enyl ester 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:

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-hex-5-enal (334968-80-8) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5S)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-methyl-oct-7-enyl ester (334968-82-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / Bu₂BOTf; DIPEA / CH₂Cl₂ / -78 °C

2: LiBH₄ / methanol; diethyl ether

3: Et₃N; DMAP

With dmap; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/ol015652m

Reference yield:

(2S,3S)-3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-1-ol (944154-96-5) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5S)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-methyl-oct-7-enyl ester (334968-82-0)

Guidance literature:

Multi-step reaction with 4 steps

1: Dess-Martin periodinane

2: 74 percent / Bu₂BOTf; DIPEA / CH₂Cl₂ / -78 °C

3: LiBH₄ / methanol; diethyl ether

4: Et₃N; DMAP

With dmap; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; 1: Dess-Martin oxidation;

DOI:10.1021/ol015652m

Reference yield:

(2R,3S)-1-((R)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hex-5-en-1-one (334968-79-5) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5S)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-methyl-oct-7-enyl ester (334968-82-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 2,6-lutidine

2: NaBH₄ / methanol; diethyl ether

3: Dess-Martin periodinane

4: 74 percent / Bu₂BOTf; DIPEA / CH₂Cl₂ / -78 °C

5: LiBH₄ / methanol; diethyl ether

6: Et₃N; DMAP

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; 3: Dess-Martin oxidation;

DOI:10.1021/ol015652m

upstream raw materials:

pivaloyl chloride

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-hex-5-enal

(2S,3S)-3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-1-ol

(2R,3S)-1-((R)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hex-5-en-1-one

Downstream raw materials:

(1S,4S,5R,6R)-1,10-Bis-benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-4-hydroxy-5-methyl-6-triethylsilanyloxy-decan-2-one

(2R,4S,5R,6R)-6-(4-Benzyloxy-butyl)-2-{(S)-benzyloxy-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-methyl}-2-methoxy-5-methyl-tetrahydro-pyran-4-ol

2,2-Dimethyl-propionic acid (R)-2-benzyloxy-2-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-ethyl ester

(S)-1-Benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-propan-2-one