(4aR,6S,7aS)-benzyl 6-hydroxymethyl-2,2-dimethyltetrahydro[1,3]dioxino[5,4-b]pyrrole-5(6H)-carboxylate

Base Information

• Chemical Name: (4aR,6S,7aS)-benzyl 6-hydroxymethyl-2,2-dimethyltetrahydro[1,3]dioxino[5,4-b]pyrrole-5(6H)-carboxylate
• CAS No.: 656827-19-9
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.373
• Mol file: 656827-19-9.mol

Synonyms:(4aR,6S,7aS)-benzyl 6-hydroxymethyl-2,2-dimethyltetrahydro[1,3]dioxino[5,4-b]pyrrole-5(6H)-carboxylate

Chemical Property of (4aR,6S,7aS)-benzyl 6-hydroxymethyl-2,2-dimethyltetrahydro[1,3]dioxino[5,4-b]pyrrole-5(6H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6S,7aS)-benzyl 6-hydroxymethyl-2,2-dimethyltetrahydro[1,3]dioxino[5,4-b]pyrrole-5(6H)-carboxylate

There total 20 articles about (4aR,6S,7aS)-benzyl 6-hydroxymethyl-2,2-dimethyltetrahydro[1,3]dioxino[5,4-b]pyrrole-5(6H)-carboxylate 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: 78.0%

C9H17NO3 (1321980-74-8) + benzyl chloroformate (501-53-1,94274-21-2) → (4aR,6S,7aS)-benzyl 6-hydroxymethyl-2,2-dimethyltetrahydro[1,3]dioxino[5,4-b]pyrrole-5(6H)-carboxylate (656827-19-9)

Guidance literature:

With sodium hydrogencarbonate; In ethyl acetate; at 0 ℃; for 1h;

DOI:10.1055/s-0030-1260546

Reference yield: 65.0%

(4S,5R)-5-(benzyloxycarbonyl)amino-2,2-dimethyl-4-(2-propenyl)-1,3-dioxane (656827-11-1) → (4aR,6S,7aS)-benzyl 6-hydroxymethyl-2,2-dimethyltetrahydro[1,3]dioxino[5,4-b]pyrrole-5(6H)-carboxylate (656827-19-9)

Guidance literature:

(4S,5R)-5-(benzyloxycarbonyl)amino-2,2-dimethyl-4-(2-propenyl)-1,3-dioxane; With mercury(II) diacetate; In acetonitrile; for 1h; Heating;

With sodium tetrahydroborate; oxygen; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1021/jo035441q

Reference yield:

(2R,3S)-2-(benzyloxycarbonyl)amino-hex-5-ene-1,3-diol (656827-17-7) → (4aR,6S,7aS)-benzyl 6-hydroxymethyl-2,2-dimethyltetrahydro[1,3]dioxino[5,4-b]pyrrole-5(6H)-carboxylate (656827-19-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / camphorsulfonic acid / acetone / 2 h / 20 °C

2.1: mercuric(II) acetate / acetonitrile / 1 h / Heating

2.2: 65 percent / O₂; NaBH₄ / dimethylformamide / 4 h / 20 °C

With camphor-10-sulfonic acid; mercury(II) diacetate; In acetone; acetonitrile;

DOI:10.1021/jo035441q

upstream raw materials:

(4S,5R)-5-(benzyloxycarbonyl)amino-2,2-dimethyl-4-(2-propenyl)-1,3-dioxane

(2R,3S)-2-(benzyloxycarbonyl)amino-hex-5-ene-1,3-diol

C₂₃H₂₈O₅

C₂₁H₂₆O₄

Downstream raw materials:

methyl (4aR,6S,7aS)-5-benzyloxycarbonyl-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrol-6-carboxylate