(4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

Base Information

• Chemical Name: (4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine
• CAS No.: 193686-94-1
• Molecular Formula: C₁₇H₁₉NO₄S
• Molecular Weight: 333.408
• Mol file: 193686-94-1.mol

Synonyms:(4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

Chemical Property of (4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

There total 4 articles about (4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 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: 40.0%

vinyl acetate (108-05-4,9003-20-7) + cis-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine → (4R,5S)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (193686-96-3) + (4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (193686-94-1) + acetic acid 5-hydroxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl ester (193686-95-2)

Guidance literature:

With Lipase QL; at 20 ℃; for 6h;

DOI:10.1016/S0040-4020(00)00388-4

Reference yield:

vinyl acetate (108-05-4,9003-20-7) + 1-(p-toluenesulfonyl)-2,3-dihydro-1H-1-benzazepine (19673-34-8) → (4R,5S)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (193686-96-3) + (4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (193686-94-1) + acetic acid 5-hydroxy-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl ester (193686-95-2)

Guidance literature:

1-(p-toluenesulfonyl)-2,3-dihydro-1H-1-benzazepine; With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃;

vinyl acetate; With Lipase QL; at 20 ℃;

DOI:10.1016/S0040-4020(00)00388-4

Reference yield:

5-hydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (19673-33-7) → (4S,5R)-4,5-dihydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (193686-94-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / p-toluenesulfonic acid / toluene / 6 h / Heating

2: 69 percent / osmium tetroxide; 4-methylmorpholine N-oxide / acetone; 2-methyl-propan-2-ol; H₂O / 20 °C

3: lipase QL / 6 h / 20 °C

With osmium(VIII) oxide; Lipase QL; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In water; acetone; toluene; tert-butyl alcohol; 1: Dehydration / 2: Oxidation / 3: Acetylation;

DOI:10.1016/S0040-4020(00)00388-4

upstream raw materials:

vinyl acetate

1-(p-toluenesulfonyl)-2,3-dihydro-1H-1-benzazepine

5-hydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

Downstream raw materials:

(4S,5R)-4-hydroxy-5-methoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine