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

Base Information

• Chemical Name: (2R,3S)-1-((R)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hex-5-en-1-one
• CAS No.: 334968-79-5
• Molecular Formula: C₁₇H₂₁NO₃S
• Molecular Weight: 319.425
• Mol file: 334968-79-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2R,3S)-1-((R)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hex-5-en-1-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: 94.0%

3-butenal (7319-38-2) + (R)-1-(4-benzyl-2-thioxooxazolidin-3-yl)propan-1-one (334968-78-4) → (2R,3S)-1-((R)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hex-5-en-1-one (334968-79-5)

Guidance literature:

With titanium tetrachloride; (-)-sparteine; In dichloromethane; at -78 - 0 ℃;

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) → (S)-Benzyloxy-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-acetaldehyde (334968-84-2)

Guidance literature:

Multi-step reaction with 10 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

7: OsO₄; NaIO₄

8: POCl₃; pyridine / 70 °C

9: i-Bu₂AlH

10: Dess-Martin periodinane

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In methanol; diethyl ether; dichloromethane; 3: Dess-Martin oxidation / 10: 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) → (S)-1-Benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-propan-2-one (334968-75-1)

Guidance literature:

Multi-step reaction with 12 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

7: OsO₄; NaIO₄

8: POCl₃; pyridine / 70 °C

9: i-Bu₂AlH

10: Dess-Martin periodinane

11: diethyl ether

12: Dess-Martin periodinane

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In methanol; diethyl ether; dichloromethane; 3: Dess-Martin oxidation / 10: Dess-Martin oxidation / 12: Dess-Martin oxidation;

DOI:10.1021/ol015652m

upstream raw materials:

3-butenal

(R)-1-(4-benzyl-2-thioxooxazolidin-3-yl)propan-1-one

Downstream raw materials:

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

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

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

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