(2S,3R,5R)-5-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-6-methoxy-2-methyl-3-triethylsilanyloxy-hexan-1-one

Base Information

• Chemical Name: (2S,3R,5R)-5-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-6-methoxy-2-methyl-3-triethylsilanyloxy-hexan-1-one
• CAS No.: 869382-52-5
• Molecular Formula: C₃₁H₄₅NO₄S₂Si
• Molecular Weight: 587.92
• Mol file: 869382-52-5.mol

Synonyms:(2S,3R,5R)-5-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-6-methoxy-2-methyl-3-triethylsilanyloxy-hexan-1-one

Chemical Property of (2S,3R,5R)-5-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-6-methoxy-2-methyl-3-triethylsilanyloxy-hexan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5R)-5-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-6-methoxy-2-methyl-3-triethylsilanyloxy-hexan-1-one

There total 6 articles about (2S,3R,5R)-5-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-6-methoxy-2-methyl-3-triethylsilanyloxy-hexan-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: 97.0%

(2S,3R,5R)-5-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxy-6-methoxy-2-methyl-hexan-1-one (869382-30-9) + triethylsilyl trifluoromethyl sulfonate (79271-56-0) → (2S,3R,5R)-5-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-6-methoxy-2-methyl-3-triethylsilanyloxy-hexan-1-one (869382-52-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1021/ja0549289

Reference yield:

((R)-1-Methoxymethyl-but-3-enyloxymethyl)-benzene → (2S,3R,5R)-5-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-6-methoxy-2-methyl-3-triethylsilanyloxy-hexan-1-one (869382-52-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: OsO₄; NMO / tetrahydrofuran; H₂O / 15 h

1.2: 60 percent / aq. NaIO₄ / tetrahydrofuran

2.1: TiCl₄ / CH₂Cl₂ / 0.33 h / cooling

2.2: (-)-sparteine / CH₂Cl₂ / 0.33 h / cooling

2.3: 90 percent / CH₂Cl₂; 1-methyl-pyrrolidin-2-one / 14 h / -30 °C

3.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

With 2,6-dimethylpyridine; osmium(VIII) oxide; N-methyl-2-indolinone; titanium tetrachloride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja0549289

Reference yield:

(4S)-4-benzyl-3-[2-(benzyloxy)acetyl]-1,3-oxazolan-2-one (236110-81-9) → (2S,3R,5R)-5-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-6-methoxy-2-methyl-3-triethylsilanyloxy-hexan-1-one (869382-52-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 75 percent / NaN(SiMe₃)2 / toluene; tetrahydrofuran / -78 - -45 °C

2.1: 85 percent / NaBH₄ / tetrahydrofuran; H₂O / 1 h

3.1: 88 percent / NaH / tetrahydrofuran / 0 - 25 °C

4.1: OsO₄; NMO / tetrahydrofuran; H₂O / 15 h

4.2: 60 percent / aq. NaIO₄ / tetrahydrofuran

5.1: TiCl₄ / CH₂Cl₂ / 0.33 h / cooling

5.2: (-)-sparteine / CH₂Cl₂ / 0.33 h / cooling

5.3: 90 percent / CH₂Cl₂; 1-methyl-pyrrolidin-2-one / 14 h / -30 °C

6.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; sodium hexamethyldisilazane; titanium tetrachloride; sodium hydride; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/ja0549289

upstream raw materials:

(2S,3R,5R)-5-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxy-6-methoxy-2-methyl-hexan-1-one

triethylsilyl trifluoromethyl sulfonate

(4S)-4-benzyl-3-[2-(benzyloxy)acetyl]-1,3-oxazolan-2-one

(R)-3-Benzyloxy-4-methoxy-butyraldehyde

Downstream raw materials:

Acetic acid (E)-(4S,5S,10R,11S,12S,13R,15R)-15-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5,16-dimethoxy-10,12-dimethyl-9-oxo-13-triethylsilanyloxy-11-trimethylsilanyloxy-hexadec-7-enyl ester

acetic acid 6-{5-[6-(2-benzyloxy-3-methoxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-2-oxo-[1,3]dioxolan-4-yl}-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-hexyl ester

Acetic acid (E)-(4S,5S)-8-[(2S,3R,4S,5S,6R)-6-((R)-2-benzyloxy-3-methoxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-oct-7-enyl ester

(2R,3S,4S,5R,7R)-7-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-8-methoxy-2,4-dimethyl-5-triethylsilanyloxy-3-trimethylsilanyloxy-octan-1-one