(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-6-(benzyloxy)-3-hydroxy-2-methylhexan-1-one

Base Information

• Chemical Name: (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-6-(benzyloxy)-3-hydroxy-2-methylhexan-1-one
• CAS No.: 1262206-03-0
• Molecular Formula: C₂₄H₂₉NO₃S₂
• Molecular Weight: 443.631
• Mol file: 1262206-03-0.mol

Synonyms:(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-6-(benzyloxy)-3-hydroxy-2-methylhexan-1-one

Chemical Property of (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-6-(benzyloxy)-3-hydroxy-2-methylhexan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-6-(benzyloxy)-3-hydroxy-2-methylhexan-1-one

There total 3 articles about (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-6-(benzyloxy)-3-hydroxy-2-methylhexan-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: 90.0%

4-benzyloxybutanal (5470-84-8) + (S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione (263764-23-4,863324-53-2) → (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-6-(benzyloxy)-3-hydroxy-2-methylhexan-1-one (1262206-03-0)

Guidance literature:

(S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione; With titanium tetrachloride; In dichloromethane; at -15 ℃; for 0.25h; Inert atmosphere;

With (-)-sparteine; In dichloromethane; at -15 ℃; for 0.5h; Inert atmosphere;

4-benzyloxybutanal; In dichloromethane; at -15 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol102658d

Reference yield:

4-benzyloxy-butan-1-ol (4541-14-4) → (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-6-(benzyloxy)-3-hydroxy-2-methylhexan-1-one (1262206-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

1.2: 1.5 h / -78 - 20 °C

2.1: titanium tetrachloride / dichloromethane / -15 °C

2.2: 0.5 h / -15 °C

2.3: 1 h / -15 °C

With oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; In dichloromethane;

DOI:10.1016/j.tetlet.2013.01.134

Reference yield:

benzyl bromide (100-39-0) → (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-6-(benzyloxy)-3-hydroxy-2-methylhexan-1-one (1262206-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 2.25 h / 0 - 20 °C

1.2: 12.25 h / 0 - 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

2.2: 1.5 h / -78 - 20 °C

3.1: titanium tetrachloride / dichloromethane / -15 °C

3.2: 0.5 h / -15 °C

3.3: 1 h / -15 °C

With oxalyl dichloride; titanium tetrachloride; sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; mineral oil;

DOI:10.1016/j.tetlet.2013.01.134

upstream raw materials:

4-benzyloxybutanal

(S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione

benzyl bromide

4-benzyloxy-butan-1-ol

Downstream raw materials:

ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate

(4S,5S,E)-ethyl 8-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methyloct-2-enoate

(4S,5S,E)-8-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methyloct-2-en-1-ol

(4S,5S)-8-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methyloctanal