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

Base Information

Chemical Name:(4aR,7S,7aS)-7-benzyloxytetrahydro-4a-hydroxy-5-(6-hydroxyhexyl)-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrol-6(4H)-one
CAS No.:1274850-37-1
Molecular Formula:C₂₁H₃₁NO₆
Molecular Weight:393.48
Hs Code.:

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

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Chemical Property of (4aR,7S,7aS)-7-benzyloxytetrahydro-4a-hydroxy-5-(6-hydroxyhexyl)-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrol-6(4H)-one

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Technology Process of (4aR,7S,7aS)-7-benzyloxytetrahydro-4a-hydroxy-5-(6-hydroxyhexyl)-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrol-6(4H)-one

There total 6 articles about (4aR,7S,7aS)-7-benzyloxytetrahydro-4a-hydroxy-5-(6-hydroxyhexyl)-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrol-6(4H)-one 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: 72.0%

: 4048-33-3
6-amino-1-hexanol

: 1274850-32-6
(4aS,7S,7aS)-7-benzyloxytetrahydro-4a-methoxy-2,2-dimethylfuro[3,2-d][1,3]dioxin-6-one

: 1274850-37-1
(4aR,7S,7aS)-7-benzyloxytetrahydro-4a-hydroxy-5-(6-hydroxyhexyl)-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrol-6(4H)-one

Guidance literature:: With toluene-4-sulfonic acid; In ethanol; at 20 ℃; diastereospecific reaction;
DOI:10.1021/jo1020322

Reference yield:

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

: 1274850-37-1
(4aR,7S,7aS)-7-benzyloxytetrahydro-4a-hydroxy-5-(6-hydroxyhexyl)-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrol-6(4H)-one

Guidance literature:: Multi-step reaction with 3 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

With sodium hydride; toluene-4-sulfonic acid; ozone; In 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

: 1274850-37-1
(4aR,7S,7aS)-7-benzyloxytetrahydro-4a-hydroxy-5-(6-hydroxyhexyl)-2,2-dimethyl[1,3]dioxino[5,4-b]pyrrol-6(4H)-one

Guidance literature:: Multi-step reaction with 4 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

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