(4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol

Base Information

• Chemical Name: (4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol
• CAS No.: 183988-98-9
• Molecular Formula: C₂₉H₃₃NO₄
• Molecular Weight: 459.585
• Mol file: 183988-98-9.mol

Synonyms:(4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol

Chemical Property of (4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol

There total 2 articles about (4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol 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:

(2S,3R,4R,5R)-1-Benzhydryl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol (132198-31-3) → (4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol (183988-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / p-TsOH / dimethylformamide

2: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 2.) DMF

With di(n-butyl)tin oxide; toluene-4-sulfonic acid; cesium fluoride; In N,N-dimethyl-formamide;

DOI:10.1021/ja960526c

Reference yield:

benzyl bromide (100-39-0) + (4aS,6R,7R,7aR)-5-Benzhydryl-6-hydroxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol (158551-04-3) → (4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol (183988-98-9)

Guidance literature:

With di(n-butyl)tin oxide; cesium fluoride; Yield given. Multistep reaction; 1.) MeOH, reflux, 2.) DMF;

DOI:10.1021/ja960526c

Reference yield: 80.0%

(4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol (183988-98-9) + 2-Trimethylsilanyl-ethanesulfonic acid ((2R,4aR,6S,7S,8R,8aR)-8-benzyloxy-7-bromo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-amide (183989-00-6) → 2-Trimethylsilanyl-ethanesulfonic acid [(2R,4aR,6R,7R,8S,8aS)-6-((4aS,6R,7R,7aR)-5-benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-yloxy)-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-amide (183989-01-7)

Guidance literature:

With potassium hexamethylsilazane; In N,N-dimethyl-formamide; at -40 - 20 ℃;

DOI:10.1021/ja960526c

upstream raw materials:

benzyl bromide

(4aS,6R,7R,7aR)-5-Benzhydryl-6-hydroxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol

(2S,3R,4R,5R)-1-Benzhydryl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol

Downstream raw materials:

2-Trimethylsilanyl-ethanesulfonic acid [(2R,4aR,6R,7R,8S,8aS)-6-((4aS,6R,7R,7aR)-5-benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-yloxy)-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-amide

2-Trimethylsilanyl-ethanesulfonic acid [(2R,3R,4R,5S,6R)-2-((4aS,6R,7R,7aR)-5-benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-amide

N-[(2R,3R,4S,5S,6R)-2-((2R,3R,4R,5S)-1-Benzhydryl-2-benzyloxymethyl-4-hydroxy-5-hydroxymethyl-pyrrolidin-3-yloxy)-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide

N-[(2R,4aR,6R,7R,8S,8aS)-6-((4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-yloxy)-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide