(2S,3S,4aR,5R,7S,8R,8aS)-7-(benzyloxy)-2,3-dimethoxy-8-((4-methoxybenzyl)oxy)-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde

Base Information

Chemical Name:(2S,3S,4aR,5R,7S,8R,8aS)-7-(benzyloxy)-2,3-dimethoxy-8-((4-methoxybenzyl)oxy)-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde
CAS No.:1392067-26-3
Molecular Formula:C₂₈H₃₆O₈
Molecular Weight:500.589
Hs Code.:

Synonyms:(2S,3S,4aR,5R,7S,8R,8aS)-7-(benzyloxy)-2,3-dimethoxy-8-((4-methoxybenzyl)oxy)-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde

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Chemical Property of (2S,3S,4aR,5R,7S,8R,8aS)-7-(benzyloxy)-2,3-dimethoxy-8-((4-methoxybenzyl)oxy)-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde

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Technology Process of (2S,3S,4aR,5R,7S,8R,8aS)-7-(benzyloxy)-2,3-dimethoxy-8-((4-methoxybenzyl)oxy)-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde

There total 10 articles about (2S,3S,4aR,5R,7S,8R,8aS)-7-(benzyloxy)-2,3-dimethoxy-8-((4-methoxybenzyl)oxy)-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde 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: 85.0%

: 1392067-16-1
1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-gulopyranose

: 1392067-26-3
(2S,3S,4aR,5R,7S,8R,8aS)-7-(benzyloxy)-2,3-dimethoxy-8-((4-methoxybenzyl)oxy)-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 21h;
DOI:10.1021/jo301240j

Reference yield:

: 1252047-54-3
(2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside

: 1392067-26-3
(2S,3S,4aR,5R,7S,8R,8aS)-7-(benzyloxy)-2,3-dimethoxy-8-((4-methoxybenzyl)oxy)-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.1: palladium dichloride / 1,4-dioxane; water / 3 h / 60 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C / Inert atmosphere

3.2: 2 h / 0 - 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

4.2: 3 h / 0 - 20 °C / Inert atmosphere

5.1: tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

6.1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C / Inert atmosphere

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 21 h / 20 °C

With n-butyllithium; potassium tert-butylate; dihydrogen peroxide; sodium hydride; sodium hydroxide; palladium dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; hexane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 3.1: |Wittig Olefination;
DOI:10.1021/jo301240j

Reference yield:

: 197577-12-1
methyl 6-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-6-iodo-α-D-mannoside

: 1392067-26-3
(2S,3S,4aR,5R,7S,8R,8aS)-7-(benzyloxy)-2,3-dimethoxy-8-((4-methoxybenzyl)oxy)-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1.1: (1S)-(+)-camphorsulfonic acid monohydrate / dichloromethane / 16 h / 20 °C

2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.1: palladium dichloride / 1,4-dioxane; water / 3 h / 60 °C / Inert atmosphere

4.1: tetrahydrofuran; toluene / 2 h / 0 - 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

5.2: 3 h / 0 - 20 °C / Inert atmosphere

6.1: tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

7.1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C / Inert atmosphere

8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 21 h / 20 °C

With (1S)-(+)-camphorsulfonic acid monohydrate; potassium tert-butylate; dihydrogen peroxide; sodium hydride; sodium hydroxide; palladium dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo301240j