[(2R,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester

Base Information

• Chemical Name: [(2R,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester
• CAS No.: 197219-86-6
• Molecular Formula: C₃₂H₃₆O₄S
• Molecular Weight: 516.701
• Mol file: 197219-86-6.mol

Synonyms:[(2R,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester

Chemical Property of [(2R,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester

There total 8 articles about [(2R,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester 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: 78.0%

((2R,3S,4R)-3,4-Bis-benzyloxy-2-phenylethynyl-tetrahydro-furan-2-yl)-thioacetic acid S-tert-butyl ester (189328-23-2) → [(2R,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester (197219-86-6)

Guidance literature:

With hydrogen; Lindlar's catalyst;

DOI:10.1016/S0040-4039(97)00380-8

Reference yield:

(2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol (171622-74-5) → [(2R,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester (197219-86-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) DMSO (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) warm to room temperature

2: 80 percent / n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

3: 1.) DMSO (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) warm to room temperature

4: 94 percent / LHMDS / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 30 min

5: 95 percent / TBAF, HF / tetrahydrofuran / Ambient temperature

6: 1.) Co₂(CO)8, 2.) BF₃*Et₂O, 3.) CAN / 1.) Et₂O, room temperature, 4 h, 2.) CH₂Cl₂, room temperature, 3 h, 3.) MeOH, 0 deg C, 25 min

7: 78 percent / Et₃N, DMAP, TsCl / CH₂Cl₂ / 3 h / Ambient temperature

With dmap; n-butyllithium; dicobalt octacarbonyl; oxalyl dichloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; hydrogen fluoride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo9711089

Reference yield:

(4R,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-ol (197219-76-4) → [(2R,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester (197219-86-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) DMSO (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) warm to room temperature

2: 94 percent / LHMDS / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 30 min

3: 95 percent / TBAF, HF / tetrahydrofuran / Ambient temperature

4: 1.) Co₂(CO)8, 2.) BF₃*Et₂O, 3.) CAN / 1.) Et₂O, room temperature, 4 h, 2.) CH₂Cl₂, room temperature, 3 h, 3.) MeOH, 0 deg C, 25 min

5: 78 percent / Et₃N, DMAP, TsCl / CH₂Cl₂ / 3 h / Ambient temperature

With dmap; dicobalt octacarbonyl; oxalyl dichloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; hydrogen fluoride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo9711089

upstream raw materials:

((2R,3S,4R)-3,4-Bis-benzyloxy-2-phenylethynyl-tetrahydro-furan-2-yl)-thioacetic acid S-tert-butyl ester

(2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol

(2S,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal

(4R,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-ol

Downstream raw materials:

3,4-bis(benzyloxy)-1,7-dioxaspiro[4.4]nonan-8-one