(2aR,4aR,5R,6S,6aS,6bR)-1-Benzyl-5-benzyloxy-6-hydroxy-hexahydro-2,4-dioxa-1-aza-cyclopenta[cd]pentalen-3-one

Base Information

Chemical Name:(2aR,4aR,5R,6S,6aS,6bR)-1-Benzyl-5-benzyloxy-6-hydroxy-hexahydro-2,4-dioxa-1-aza-cyclopenta[cd]pentalen-3-one
CAS No.:748793-15-9
Molecular Formula:C₂₁H₂₁NO₅
Molecular Weight:367.401
Hs Code.:

Synonyms:(2aR,4aR,5R,6S,6aS,6bR)-1-Benzyl-5-benzyloxy-6-hydroxy-hexahydro-2,4-dioxa-1-aza-cyclopenta[cd]pentalen-3-one

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Chemical Property of (2aR,4aR,5R,6S,6aS,6bR)-1-Benzyl-5-benzyloxy-6-hydroxy-hexahydro-2,4-dioxa-1-aza-cyclopenta[cd]pentalen-3-one

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Technology Process of (2aR,4aR,5R,6S,6aS,6bR)-1-Benzyl-5-benzyloxy-6-hydroxy-hexahydro-2,4-dioxa-1-aza-cyclopenta[cd]pentalen-3-one

There total 6 articles about (2aR,4aR,5R,6S,6aS,6bR)-1-Benzyl-5-benzyloxy-6-hydroxy-hexahydro-2,4-dioxa-1-aza-cyclopenta[cd]pentalen-3-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: 44.0%

: 622-30-0
N-benzyl hydroxylalmine

: 108266-98-4
methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-enofuranuronate

: 748793-15-9
(2aR,4aR,5R,6S,6aS,6bR)-1-Benzyl-5-benzyloxy-6-hydroxy-hexahydro-2,4-dioxa-1-aza-cyclopenta[cd]pentalen-3-one

Guidance literature:: methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-enofuranuronate; With sulfuric acid; In water; acetonitrile; at 20 ℃; for 24h;

N-benzyl hydroxylalmine; In benzene; for 4h; Further stages.; Heating;
DOI:10.1016/j.tetlet.2004.06.017

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 748793-15-9
(2aR,4aR,5R,6S,6aS,6bR)-1-Benzyl-5-benzyloxy-6-hydroxy-hexahydro-2,4-dioxa-1-aza-cyclopenta[cd]pentalen-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaIO₄ / ethanol; H₂O / 1 h

2.1: 42 percent / benzene / 4 h / Heating

3.1: H₂SO₄ / acetonitrile; H₂O / 24 h / 20 °C

3.2: 44 percent / benzene / 4 h / Heating

With sodium periodate; sulfuric acid; In ethanol; water; acetonitrile; benzene;
DOI:10.1016/j.tetlet.2004.06.017

Reference yield:

: 100-39-0
benzyl bromide

: 748793-15-9
(2aR,4aR,5R,6S,6aS,6bR)-1-Benzyl-5-benzyloxy-6-hydroxy-hexahydro-2,4-dioxa-1-aza-cyclopenta[cd]pentalen-3-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaOH; n-Bu₄NBr / CH₂Cl₂; H₂O / 16 h / 20 °C

2.1: AcOH / H₂O / 18 h / 20 °C

3.1: NaIO₄ / ethanol; H₂O / 1 h

4.1: 42 percent / benzene / 4 h / Heating

5.1: H₂SO₄ / acetonitrile; H₂O / 24 h / 20 °C

5.2: 44 percent / benzene / 4 h / Heating

With sodium hydroxide; sodium periodate; sulfuric acid; tetrabutylammomium bromide; acetic acid; In ethanol; dichloromethane; water; acetonitrile; benzene;
DOI:10.1016/j.tetlet.2004.06.017