(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

Base Information

• Chemical Name: (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
• CAS No.: 869382-53-6
• Molecular Formula: C₃₇H₅₉NO₅S₂Si₂
• Molecular Weight: 718.182
• Mol file: 869382-53-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 9 articles about (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 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: 79.0%

(2R,3S,4R,5R,7R)-7-Benzyloxy-1-((S)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxy-8-methoxy-2,4-dimethyl-5-triethylsilanyloxy-octan-1-one (869382-32-1) + chloro-trimethyl-silane (75-77-4) → (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 (869382-53-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/ja0549289

Reference yield:

((R)-1-Methoxymethyl-but-3-enyloxymethyl)-benzene → (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 (869382-53-6)

Guidance literature:

Multi-step reaction with 6 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

4.1: 86 percent / i-Bu₂AlH / CH₂Cl₂; heptane / -78 °C

5.1: TiCl₄ / CH₂Cl₂ / 0.33 h / cooling

5.2: i-Pr₂NEt / CH₂Cl₂ / 0.33 h / cooling

5.3: 62 percent / CH₂Cl₂ / 13 h / -30 °C

6.1: 79 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 0 °C

With 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; titanium tetrachloride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; n-heptane; dichloromethane; water;

DOI:10.1021/ja0549289

Reference yield:

(2S,3R,5R)-5-Benzyloxy-6-methoxy-2-methyl-3-triethylsilanyloxy-hexanal (869382-31-0) → (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 (869382-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TiCl₄ / CH₂Cl₂ / 0.33 h / cooling

1.2: i-Pr₂NEt / CH₂Cl₂ / 0.33 h / cooling

1.3: 62 percent / CH₂Cl₂ / 13 h / -30 °C

2.1: 79 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 0 °C

With dmap; titanium tetrachloride; triethylamine; In dichloromethane;

DOI:10.1021/ja0549289

upstream raw materials:

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

chloro-trimethyl-silane

(2S,3R,5R)-5-Benzyloxy-6-methoxy-2-methyl-3-triethylsilanyloxy-hexanal

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

Downstream raw materials:

((3R,4S,5S,6R,8R)-8-Benzyloxy-9-methoxy-3,5-dimethyl-2-oxo-6-triethylsilanyloxy-4-trimethylsilanyloxy-nonyl)-phosphonic acid dimethyl ester

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

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