(1R,3R,4S,7R,8R,11R)-8-(4-chlorophenyl)-4-methyl-3,11-diphenyl-2,9-dioxa-10-thia-5-azatricyclo[5.2.2.0^1,5]undecan-6-one

Base Information

• Chemical Name: (1R,3R,4S,7R,8R,11R)-8-(4-chlorophenyl)-4-methyl-3,11-diphenyl-2,9-dioxa-10-thia-5-azatricyclo[5.2.2.0^1,5]undecan-6-one
• CAS No.: 599199-35-6
• Molecular Formula: C₂₆H₂₂ClNO₃S
• Molecular Weight: 463.985

Synonyms:(1R,3R,4S,7R,8R,11R)-8-(4-chlorophenyl)-4-methyl-3,11-diphenyl-2,9-dioxa-10-thia-5-azatricyclo[5.2.2.0^1,5]undecan-6-one

Chemical Property of (1R,3R,4S,7R,8R,11R)-8-(4-chlorophenyl)-4-methyl-3,11-diphenyl-2,9-dioxa-10-thia-5-azatricyclo[5.2.2.0^1,5]undecan-6-one

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Technology Process of (1R,3R,4S,7R,8R,11R)-8-(4-chlorophenyl)-4-methyl-3,11-diphenyl-2,9-dioxa-10-thia-5-azatricyclo[5.2.2.0^1,5]undecan-6-one

There total 3 articles about (1R,3R,4S,7R,8R,11R)-8-(4-chlorophenyl)-4-methyl-3,11-diphenyl-2,9-dioxa-10-thia-5-azatricyclo[5.2.2.0^1,5]undecan-6-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:

4-chlorobenzaldehyde (104-88-1) + (4S,5R)-4-methyl-5-phenyl-3-[(E)-phenylprop-2-enoyl]-1,3-oxazolidine-2-thione (599164-43-9) → (1R,3R,4S,7R,8S,11R)-8-(4-chlorophenyl)-4-methyl-3,11-diphenyl-2,9-dioxa-10-thia-5-azatricyclo[5.2.2.01,5]undecan-6-one + (1R,3R,4S,7R,8R,11R)-8-(4-chlorophenyl)-4-methyl-3,11-diphenyl-2,9-dioxa-10-thia-5-azatricyclo[5.2.2.01,5]undecan-6-one (599199-35-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -40 ℃; for 24h; Title compound not separated from byproducts;

DOI:10.1002/anie.200351106

Reference yield:

(4S,5R)-4-methyl-5-phenyl-1,3-oxazolidine-2-thione (191043-26-2) → (1R,3R,4S,7R,8R,11R)-8-(4-chlorophenyl)-4-methyl-3,11-diphenyl-2,9-dioxa-10-thia-5-azatricyclo[5.2.2.01,5]undecan-6-one (599199-35-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / pyridine / benzene / 23 h / 20 °C

2: BF₃*OEt₂ / CH₂Cl₂ / 24 h / -40 °C

With pyridine; boron trifluoride diethyl etherate; In dichloromethane; benzene; 2: tandem Michael-aldol reaction;

DOI:10.1002/chem.200501435

Reference yield:

Cinnamoyl chloride (102-92-1,17082-09-6) → (1R,3R,4S,7R,8R,11R)-8-(4-chlorophenyl)-4-methyl-3,11-diphenyl-2,9-dioxa-10-thia-5-azatricyclo[5.2.2.01,5]undecan-6-one (599199-35-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / pyridine / benzene / 23 h / 20 °C

2: BF₃*OEt₂ / CH₂Cl₂ / 24 h / -40 °C

With pyridine; boron trifluoride diethyl etherate; In dichloromethane; benzene; 2: tandem Michael-aldol reaction;

DOI:10.1002/chem.200501435

upstream raw materials:

4-chlorobenzaldehyde

(4S,5R)-4-methyl-5-phenyl-3-[(E)-phenylprop-2-enoyl]-1,3-oxazolidine-2-thione

(4S,5R)-4-methyl-5-phenyl-1,3-oxazolidine-2-thione

Cinnamoyl chloride

Downstream raw materials:

(4S,5R,2'R,3'R,1''R)-3-[3'-(4-chlorophenyl)-3'-hydroxy-2'-(1''-sulfanyl-1''-phenylmethyl)propionyl]-4-methyl-5-phenyloxazolidin-2-one

(4S,5R,2'R,3'R,1''R)-3-[3'-(4-chlorophenyl)-3'-hydroxy-2'-(1''-methylsulfanyl-1''-phenylmethyl)propionyl]-4-methyl-5-phenyloxazolidin-2-one

(4S,5R,2'R,3'R,1''R)-3-[3'-(4-chlorophenyl)-2'-(1''-methylsulfanyl-1''-phenylmethyl)-3'-trimethylsilanyloxypropionyl]-4-methyl-5-phenyloxazolidin-2-one

(4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one

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