(4aS,7R,7aR)-5-(4-methoxybenzyl)-7-benzyloxyhexahydro-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrole

Base Information

Chemical Name:(4aS,7R,7aR)-5-(4-methoxybenzyl)-7-benzyloxyhexahydro-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrole
CAS No.:1274850-49-5
Molecular Formula:C₂₃H₂₉NO₄
Molecular Weight:383.488
Hs Code.:

Synonyms:(4aS,7R,7aR)-5-(4-methoxybenzyl)-7-benzyloxyhexahydro-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrole

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Chemical Property of (4aS,7R,7aR)-5-(4-methoxybenzyl)-7-benzyloxyhexahydro-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrole

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Technology Process of (4aS,7R,7aR)-5-(4-methoxybenzyl)-7-benzyloxyhexahydro-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrole

There total 6 articles about (4aS,7R,7aR)-5-(4-methoxybenzyl)-7-benzyloxyhexahydro-2,2-dimethyl[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: 95.0%

: 1274850-42-8
(4aR,7S,7aS)-5-(4-methoxybenzyl)-7-benzyloxytetrahydro-4a-hydroxy-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrol-6(4H)-one

: 1274850-49-5
(4aS,7R,7aR)-5-(4-methoxybenzyl)-7-benzyloxyhexahydro-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrole

Guidance literature:: With aluminium hydride; In tetrahydrofuran; at -78 - 20 ℃; for 1.33333h; Inert atmosphere;
DOI:10.1021/jo1020322

Reference yield:

: 909801-51-0
methyl 6-deoxy-6-iodo-1,3-O-isopropylidene-α-D-fructofuranoside

: 1274850-49-5
(4aS,7R,7aR)-5-(4-methoxybenzyl)-7-benzyloxyhexahydro-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrole

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

1.2: 5 h / 0 °C / Inert atmosphere

2.1: ozone / methanol / -78 °C

2.2: 2 h / -78 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / ethanol / 20 °C

4.1: aluminium hydride / tetrahydrofuran / 1.33 h / -78 - 20 °C / Inert atmosphere

With aluminium hydride; sodium hydride; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jo1020322

Reference yield:

: 80817-67-0
methyl 1,3-O-isopropylidene-α-D-fructofuranoside

: 1274850-49-5
(4aS,7R,7aR)-5-(4-methoxybenzyl)-7-benzyloxyhexahydro-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrole

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / Reflux

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

2.2: 5 h / 0 °C / Inert atmosphere

3.1: ozone / methanol / -78 °C

3.2: 2 h / -78 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / ethanol / 20 °C

5.1: aluminium hydride / tetrahydrofuran / 1.33 h / -78 - 20 °C / Inert atmosphere

With 1H-imidazole; aluminium hydride; iodine; sodium hydride; toluene-4-sulfonic acid; ozone; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jo1020322