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

Base Information

• Chemical Name: 6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-gulopyranoside
• CAS No.: 1392067-34-3
• Molecular Formula: C₃₀H₄₀O₉
• Molecular Weight: 544.642

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

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

There total 9 articles about 6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-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: 99.0%

1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-gulopyranose (1392067-16-1) + acetic anhydride (108-24-7) → 6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-gulopyranoside (1392067-34-3)

Guidance literature:

With pyridine; at 20 ℃; for 17h;

DOI:10.1021/jo301240j

Reference yield:

methyl 6-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-6-iodo-α-D-mannoside (197577-12-1) → 6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-gulopyranoside (1392067-34-3)

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: pyridine / 17 h / 20 °C

With pyridine; (1S)-(+)-camphorsulfonic acid monohydrate; potassium tert-butylate; dihydrogen peroxide; sodium hydride; sodium hydroxide; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo301240j

Reference yield:

(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 (176897-12-4) → 6-O-acetyl-1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-gulopyranoside (1392067-34-3)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; 1H-imidazole; (1S)-(+)-camphorsulfonic acid monohydrate; potassium tert-butylate; dihydrogen peroxide; iodine; sodium hydride; triphenylphosphine; sodium hydroxide; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo301240j

upstream raw materials:

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

(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

6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside

benzyl 6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside

Downstream raw materials:

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

6-O-acetyl-2-azido-1-O-Benzyl-2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-β-L-gulopyranoside

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