Toluene-4-sulfonic acid (2S,3R)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2S,3R)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester
• CAS No.: 181534-74-7
• Molecular Formula: C₃₃H₄₀O₇SSi
• Molecular Weight: 608.828
• Mol file: 181534-74-7.mol

Synonyms:Toluene-4-sulfonic acid (2S,3R)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester

Chemical Property of Toluene-4-sulfonic acid (2S,3R)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2S,3R)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester

There total 6 articles about Toluene-4-sulfonic acid (2S,3R)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl 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: 96.0%

p-toluenesulfonyl chloride (98-59-9) + (5R,6R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-hydroxy-5,6-dihydro-pyran-2-one (181534-68-9) → Toluene-4-sulfonic acid (2S,3R)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester (181534-74-7)

Guidance literature:

With dmap; In dichloromethane; for 1.5h;

DOI:10.1021/jo970725u

Reference yield:

(R)-5-[(1R,2S,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-phenyl-propyl]-5H-furan-2-one (153000-32-9) → Toluene-4-sulfonic acid (2S,3R)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester (181534-74-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / CH₂Cl₂ / 10 h / Ambient temperature

2: DIBALH / diethyl ether / 0.17 h / -78 °C

4: 96 percent / DMAP / CH₂Cl₂ / 1.5 h

With dmap; diisobutylaluminium hydride; In diethyl ether; dichloromethane;

DOI:10.1021/jo970725u

Reference yield:

(R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one (181534-66-7) → Toluene-4-sulfonic acid (2S,3R)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester (181534-74-7)

Guidance literature:

Multi-step reaction with 3 steps

1: DIBALH / diethyl ether / 0.17 h / -78 °C

3: 96 percent / DMAP / CH₂Cl₂ / 1.5 h

With dmap; diisobutylaluminium hydride; In diethyl ether; dichloromethane;

DOI:10.1021/jo970725u

upstream raw materials:

p-toluenesulfonyl chloride

(5R,6R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-hydroxy-5,6-dihydro-pyran-2-one

(R)-5-[(1R,2S,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-phenyl-propyl]-5H-furan-2-one

(R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one

Downstream raw materials:

goniothalenol

(4S,4aS,6R,7R,7aS)-4,7-dihydroxy-6-phenyl-1,5-dioxabicyclo[4.3.0]nonan-2-one

(2R,3R,3aS,6S,7R,7aS)-3-Benzyloxy-6,7-dihydroxy-2-phenyl-hexahydro-furo[3,2-b]pyran-5-one

(2R,3R,3aS,7R,7aS)-3,7-dihydroxy-2-phenyltetrahydro-2H-furo[3,2-b]pyran-5(6H)-one