(4aR,6S,7aS)-6-(benzyloxymethyl)-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrole

Base Information

• Chemical Name: (4aR,6S,7aS)-6-(benzyloxymethyl)-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrole
• CAS No.: 1321980-73-7
• Molecular Formula: C₁₆H₂₃NO₃
• Molecular Weight: 277.364
• Mol file: 1321980-73-7.mol

Synonyms:

Chemical Property of (4aR,6S,7aS)-6-(benzyloxymethyl)-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6S,7aS)-6-(benzyloxymethyl)-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrole

There total 13 articles about (4aR,6S,7aS)-6-(benzyloxymethyl)-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrole 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:

C19H24O4 (1321980-61-3) → (4aR,6S,7aS)-6-(benzyloxymethyl)-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrole (1321980-73-7)

Guidance literature:

Multi-step reaction with 9 steps

1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 3 h / 0 - 20 °C

2: dichloromethane / 2 h / 20 °C

3: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 - -10 °C

4: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / dichloromethane / 20 h / -20 °C

5: sodium azide; Trimethyl borate / N,N-dimethyl-formamide / 3.5 h / 90 °C

6: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C

7: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 5 h / 20 °C

8: diisopropylamine / 4.5 h / 0 - 20 °C

9: indium; ammonium chloride; triethylamine / methanol / 6 h / Reflux

With titanium(IV) isopropylate; tert.-butylhydroperoxide; indium; sodium azide; Trimethyl borate; L-(+)-diisopropyl tartrate; water; diisobutylaluminium hydride; ammonium chloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Swern oxidation / 4: Sharpless epoxidation;

DOI:10.1055/s-0030-1260546

Reference yield:

C21H26O4 (1321980-63-5) → (4aR,6S,7aS)-6-(benzyloxymethyl)-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrole (1321980-73-7)

Guidance literature:

Multi-step reaction with 6 steps

1: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / dichloromethane / 20 h / -20 °C

2: sodium azide; Trimethyl borate / N,N-dimethyl-formamide / 3.5 h / 90 °C

3: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C

4: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 5 h / 20 °C

5: diisopropylamine / 4.5 h / 0 - 20 °C

6: indium; ammonium chloride; triethylamine / methanol / 6 h / Reflux

With titanium(IV) isopropylate; tert.-butylhydroperoxide; indium; sodium azide; Trimethyl borate; L-(+)-diisopropyl tartrate; water; ammonium chloride; toluene-4-sulfonic acid; triethylamine; diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Sharpless epoxidation;

DOI:10.1055/s-0030-1260546

Reference yield:

2-azido-6-(benzyloxy)-5-(4-methoxybenzyloxy)hexane-1,3-diol (1321980-67-9) → (4aR,6S,7aS)-6-(benzyloxymethyl)-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrole (1321980-73-7)

Guidance literature:

Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C

2: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 5 h / 20 °C

3: diisopropylamine / 4.5 h / 0 - 20 °C

4: indium; ammonium chloride; triethylamine / methanol / 6 h / Reflux

With indium; water; ammonium chloride; toluene-4-sulfonic acid; triethylamine; diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane;

DOI:10.1055/s-0030-1260546

upstream raw materials:

C₁₉H₂₄O₄

C₂₃H₂₈O₅

C₂₁H₂₆O₄

(3-{3-(benzyloxy)-2-[(4-methoxybenzyl)oxy]propyl}oxiran-2-yl)methanol

Downstream raw materials:

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