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

Base Information

• Chemical Name: methyl (4aR,6S,7aS)-5-benzyloxycarbonyl-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrol-6-carboxylate
• CAS No.: 656827-21-3
• Molecular Formula: C₁₈H₂₃NO₆
• Molecular Weight: 349.384
• Mol file: 656827-21-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about methyl (4aR,6S,7aS)-5-benzyloxycarbonyl-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrol-6-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:

1-[(4R)-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl]-but-3-en-1-ol → methyl (4aR,6S,7aS)-5-benzyloxycarbonyl-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrol-6-carboxylate (656827-21-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2.4 g / acetic acid / H₂O / 20 °C

2.1: 92 percent / camphorsulfonic acid / acetone / 2 h / 20 °C

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

3.2: 65 percent / O₂; NaBH₄ / dimethylformamide / 4 h / 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂

5.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.5 h / 20 °C

6.1: 0.528 g / diethyl ether / 0.5 h

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; camphor-10-sulfonic acid; mercury(II) diacetate; Dess-Martin periodane; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo035441q

Reference yield:

(2R,3S)-2-(benzyloxycarbonyl)amino-hex-5-ene-1,3-diol (656827-17-7) → methyl (4aR,6S,7aS)-5-benzyloxycarbonyl-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrol-6-carboxylate (656827-21-3)

Guidance literature:

Multi-step reaction with 5 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

3.1: Dess-Martin periodinane / CH₂Cl₂

4.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.5 h / 20 °C

5.1: 0.528 g / diethyl ether / 0.5 h

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; camphor-10-sulfonic acid; mercury(II) diacetate; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo035441q

Reference yield:

(4S,5R)-5-(benzyloxycarbonyl)amino-2,2-dimethyl-4-(2-propenyl)-1,3-dioxane (656827-11-1) → methyl (4aR,6S,7aS)-5-benzyloxycarbonyl-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrol-6-carboxylate (656827-21-3)

Guidance literature:

Multi-step reaction with 4 steps

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

1.2: 65 percent / O₂; NaBH₄ / dimethylformamide / 4 h / 20 °C

2.1: Dess-Martin periodinane / CH₂Cl₂

3.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.5 h / 20 °C

4.1: 0.528 g / diethyl ether / 0.5 h

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; mercury(II) diacetate; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo035441q

upstream raw materials:

diazomethane

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

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

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