(4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene

Base Information

• Chemical Name: (4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene
• CAS No.: 179536-77-7
• Molecular Formula: C₂₀H₂₉NO₄S
• Molecular Weight: 379.521
• Mol file: 179536-77-7.mol

Synonyms:(4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene

Chemical Property of (4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene

There total 6 articles about (4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene 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: 94.0%

(4aS,6S,8aR)-6-((E)-5-Benzenesulfonyl-pent-4-enyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid trityl ester → (4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene (179536-77-7)

Guidance literature:

With ammonium acetate; 10% Cd/Pd; In tetrahydrofuran; for 48h; Ambient temperature;

DOI:10.1021/jo9608174

Reference yield: 94.0%

(4aS,6S,8aR)-6-((E)-5-Benzenesulfonyl-pent-4-enyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl ester (179536-76-6) → (4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene (179536-77-7)

Guidance literature:

10% Cd/Pd;

DOI:10.1021/ja9925958

Reference yield:

diethyl phenylsulfonylmethylphosphonate (56069-39-7) → (4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene (179536-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) Swern reagent, 2) NaH / 2) THF

2: 94 percent / NH₄OAc / 10percent Cd-Pb / tetrahydrofuran / 48 h / Ambient temperature

With swern reagent; ammonium acetate; sodium hydride; 10% Cd/Pd; In tetrahydrofuran;

DOI:10.1021/jo9608174

upstream raw materials:

(4aS,6S,8aR)-6-((E)-5-Benzenesulfonyl-pent-4-enyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid 2,2,2-trichloro-ethyl ester

diethyl phenylsulfonylmethylphosphonate

2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol

ethyl (4aS,6R,8aR)-(+)-hexahydro-2,2-dimethyl-5-(phenylmethyl)-4H-1,3-dioxino-[5,4-b]pyridine-6-but-(2E)-enoate

Downstream raw materials:

(3R,4S,6S,9aS)-(-)-4-{[(2,2-dimethylethyl)diphenylsiloxy]methyl}-3-hydroxy-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine

(3R,4S,6S,9aS)-6-Benzenesulfonylmethyl-4-hydroxymethyl-octahydro-quinolizin-3-ol

(3R,4S,6S,9aS)-(-)-{[(2,2-dimethyl)diphenylsiloxy]methyl}-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)octahydro-2H-quinolizine

(3R,4S,6S,9aS)-(-)-4-(hydroxymethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine