6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5acarba-β-L-gulopyranoside

Base Information

Chemical Name:6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5acarba-β-L-gulopyranoside
CAS No.:1392067-36-5
Molecular Formula:C₂₂H₃₂O₈
Molecular Weight:424.491
Hs Code.:

Synonyms:6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5acarba-β-L-gulopyranoside

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Chemical Property of 6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5acarba-β-L-gulopyranoside

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Technology Process of 6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5acarba-β-L-gulopyranoside

There total 10 articles about 6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5acarba-β-L-gulopyranoside 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: 87.0%

: 1392067-34-3
6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-gulopyranoside

: 1392067-36-5
6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5acarba-β-L-gulopyranoside

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 - 20 ℃; for 2.66667h;
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

: 1392067-36-5
6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5acarba-β-L-gulopyranoside

Guidance literature:: Multi-step reaction with 9 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: pyridine / 17 h / 20 °C

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2.67 h / 0 - 20 °C

With pyridine; (1S)-(+)-camphorsulfonic acid monohydrate; potassium tert-butylate; dihydrogen peroxide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo301240j

Reference yield:

: 176897-12-4
(2S,3S,4aR,5R,7S,8S,8aR)-5-(hydroxymethyl)-2,3,7-trimethoxy-2,3-dimethylhexahydro-2Hpyrano[3,4-b][1,4]dioxin-8-ol4

: 1392067-36-5
6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5acarba-β-L-gulopyranoside

Guidance literature:: Multi-step reaction with 10 steps

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

2.1: (1S)-(+)-camphorsulfonic acid monohydrate / dichloromethane / 16 h / 20 °C

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

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

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

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

6.2: 3 h / 0 - 20 °C / Inert atmosphere

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

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

9.1: pyridine / 17 h / 20 °C

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

With pyridine; 1H-imidazole; (1S)-(+)-camphorsulfonic acid monohydrate; potassium tert-butylate; dihydrogen peroxide; iodine; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo301240j