(S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione

Base Information

• Chemical Name: (S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione
• CAS No.: 876954-51-7
• Molecular Formula: C₂₆H₄₃NO₃S₂Si
• Molecular Weight: 509.85
• Mol file: 876954-51-7.mol

Synonyms:(S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione

Chemical Property of (S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione

There total 1 articles about (S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione 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: 60.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2S)-3-(benzyloxy)-2-methylpropanal (79027-28-4) + (4S)-4-isopropyl-3-(1-oxopropyl)-1,3-thiazolidine-2-thione (102831-92-5,487029-68-5) → (S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione (876954-51-7)

Guidance literature:

(4S)-4-isopropyl-3-(1-oxopropyl)-1,3-thiazolidine-2-thione; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - -50 ℃; for 2.5h;

(2S)-3-(benzyloxy)-2-methylpropanal; In dichloromethane; at -78 - 0 ℃; for 2.75h;

t-butyldimethylsiyl triflate; With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.75h;

DOI:10.1021/ol052900w

Reference yield: 93.0%

(S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione (876954-51-7) → (2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal (444109-42-6)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.166667h;

DOI:10.1021/ol052900w

Reference yield:

(S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione (876954-51-7) → (R)-2-{(2R,5S,6R)-6-[(1S,2R,3R,5R,6S,7S,9R)-10-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-5-ethyl-2-hydroxy-1,3,7,9-tetramethyl-4-oxo-decyl]-5-methyl-tetrahydro-pyran-2-yl}-butyric acid methyl ester

Guidance literature:

Multi-step reaction with 9 steps

1.1: 93 percent / DIBALH / hexane; CH₂Cl₂ / 0.17 h / -78 °C

2.1: 18-crown-6; K₂CO₃ / toluene / 4 h / -20 - 0 °C

2.2: 176 mg / aq. HCl / methanol / 15 h / 20 °C

3.1: DIBALH / hexane; CH₂Cl₂ / 0.83 h / -78 °C

4.1: PPTS / 2 h / 20 °C

5.1: TiCl₄; iPr₂NEt / CH₂Cl₂ / -78 - -50 °C

5.2: SnCl₄ / CH₂Cl₂ / 16.5 h / -78 - -20 °C

6.1: 135 mg / DMAP / 64 h / 20 °C

7.1: H₂ / PtO₂ / methanol / 0.5 h / 20 °C / 760 Torr

7.2: 83 percent / H₂ / Pd/C / methanol / 5 h / 20 °C / 760 Torr

8.1: oxalyl chloride; DMSO; iPr₂NEt / CH₂Cl₂ / -78 - 0 °C

9.1: n-BuLi; 2,2,6,6-tetramethylpiperidine / hexane; tetrahydrofuran / 3 h / -78 °C

9.2: 6 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

With 2,2,6,6-tetramethyl-piperidine; dmap; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; hydrogen; pyridinium p-toluenesulfonate; titanium tetrachloride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 8.1: Swern oxidation;

DOI:10.1021/ol052900w

upstream raw materials:

t-butyldimethylsiyl triflate

(2S)-3-(benzyloxy)-2-methylpropanal

(4S)-4-isopropyl-3-(1-oxopropyl)-1,3-thiazolidine-2-thione

Downstream raw materials:

(2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal

(5S,6R)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-5-methyl-5,6-dihydro-2H-pyran-2-ol

(5S,6R)-6-[(1S)-2-benzyloxy-1-methyl-ethyl]-5-methyl-5,6-dihydro-pyran-2-one

(2R,3S)-2-[(S)-1-benzyloxypropan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran