3,4,6-tri-O-acetyl-2-acetamido-1-O-benzyl-2-deoxy-5a-carba-α-D-glucopyranose

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Chemical Name:3,4,6-tri-O-acetyl-2-acetamido-1-O-benzyl-2-deoxy-5a-carba-α-D-glucopyranose
CAS No.:1392067-01-4
Molecular Formula:C₂₂H₂₉NO₈
Molecular Weight:435.474
Hs Code.:

Synonyms:3,4,6-tri-O-acetyl-2-acetamido-1-O-benzyl-2-deoxy-5a-carba-α-D-glucopyranose

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Chemical Property of 3,4,6-tri-O-acetyl-2-acetamido-1-O-benzyl-2-deoxy-5a-carba-α-D-glucopyranose

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Technology Process of 3,4,6-tri-O-acetyl-2-acetamido-1-O-benzyl-2-deoxy-5a-carba-α-D-glucopyranose

There total 14 articles about 3,4,6-tri-O-acetyl-2-acetamido-1-O-benzyl-2-deoxy-5a-carba-α-D-glucopyranose 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:

: 617-04-9
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

: 1392067-01-4
3,4,6-tri-O-acetyl-2-acetamido-1-O-benzyl-2-deoxy-5a-carba-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 17 steps

1.1: (1S)-10-camphorsulfonic acid / methanol / 17 h / Reflux

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

3.1: (1S)-(+)-camphorsulfonic acid monohydrate / dichloromethane / 16 h / 20 °C

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

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

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

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

7.2: 3 h / 0 - 20 °C / Inert atmosphere

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

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

10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 21 h / 20 °C

11.1: pyridine / methanol / 72 h / 60 °C

12.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2.67 h / 0 - 20 °C

13.1: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

14.1: N,N-dimethyl-formamide / 13.5 h / 80 °C / Darkness

15.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.25 h / 0 - 20 °C / Inert atmosphere

16.1: hydrogenchloride / methanol; water / 4 h / 20 °C

17.1: pyridine / 13 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; (1S)-(+)-camphorsulfonic acid monohydrate; (1S)-10-camphorsulfonic acid; potassium tert-butylate; dihydrogen peroxide; iodine; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; palladium dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo301240j

Reference yield:

: 1392067-14-9
(2S,3S,4aS,7S,8R,8aR)-7-hydroxy-2,3-dimethoxy-8-((pmethoxybenzyl)oxy)-2,3-dimethylhexahydrobenzo[b][1,4]dioxin-5-(4aH)-one

: 1392067-01-4
3,4,6-tri-O-acetyl-2-acetamido-1-O-benzyl-2-deoxy-5a-carba-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 12 steps

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

1.2: 2 h / 0 - 20 °C / Inert atmosphere

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

2.2: 3 h / 0 - 20 °C / Inert atmosphere

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

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

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 21 h / 20 °C

6.1: pyridine / methanol / 72 h / 60 °C

7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2.67 h / 0 - 20 °C

8.1: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

9.1: N,N-dimethyl-formamide / 13.5 h / 80 °C / Darkness

10.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.25 h / 0 - 20 °C / Inert atmosphere

11.1: hydrogenchloride / methanol; water / 4 h / 20 °C

12.1: pyridine / 13 h / 20 °C

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; dihydrogen peroxide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: |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

: 1392067-01-4
3,4,6-tri-O-acetyl-2-acetamido-1-O-benzyl-2-deoxy-5a-carba-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 15 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

9.1: pyridine / methanol / 72 h / 60 °C

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2.67 h / 0 - 20 °C

11.1: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

12.1: N,N-dimethyl-formamide / 13.5 h / 80 °C / Darkness

13.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.25 h / 0 - 20 °C / Inert atmosphere

14.1: hydrogenchloride / methanol; water / 4 h / 20 °C

15.1: pyridine / 13 h / 20 °C

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; (1S)-(+)-camphorsulfonic acid monohydrate; potassium tert-butylate; dihydrogen peroxide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; palladium dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo301240j