3,4-di-O-(p-methoxybenzyl)-5a-carba-D-glucal

Base Information

• Chemical Name: 3,4-di-O-(p-methoxybenzyl)-5a-carba-D-glucal
• CAS No.: 1334652-29-7
• Molecular Formula: C₂₃H₂₈O₅
• Molecular Weight: 384.472
• Mol file: 1334652-29-7.mol

Synonyms:3,4-di-O-(p-methoxybenzyl)-5a-carba-D-glucal

Chemical Property of 3,4-di-O-(p-methoxybenzyl)-5a-carba-D-glucal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-(p-methoxybenzyl)-5a-carba-D-glucal

There total 7 articles about 3,4-di-O-(p-methoxybenzyl)-5a-carba-D-glucal 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:

C23H26O5 → 3,4-di-O-(p-methoxybenzyl)-5a-carba-D-glucal (1334652-29-7)

Guidance literature:

C₂₃H₂₆O₅; With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 20 ℃; for 0.333333h; Inert atmosphere;

With water; In dichloromethane; Inert atmosphere;

DOI:10.1002/chir.21003

Reference yield:

6-O-(tetrahydropyran-2-yl)-D-glucal (1033614-25-3) → 3,4-di-O-(p-methoxybenzyl)-5a-carba-D-glucal (1334652-29-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 0.5 h / 20 °C / Inert atmosphere

1.2: 12 h / 0 - 20 °C / Inert atmosphere

2.1: water; acetic acid / tetrahydrofuran / 12 h / 50 °C / Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 5 h / 45 °C / Inert atmosphere

4.1: potassium hexamethylsilazane / tetrahydrofuran / 1.5 h / -78 - 0 °C / Inert atmosphere

4.2: 5 h / -78 - 20 °C / Inert atmosphere

5.1: 1,3-Dichlorobenzene / 0.33 h / 240 °C / Inert atmosphere

6.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 0.33 h / 20 °C / Inert atmosphere

6.2: Inert atmosphere

With sodium tetrahydroborate; water; potassium hexamethylsilazane; sodium hydride; acetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile; paraffin oil; 1,3-Dichlorobenzene; 4.2: Wittig reaction / 5.1: Claisen rearrangement;

DOI:10.1002/chir.21003

Reference yield:

3,4-di-O-(p-methoxybenzyl)-D-glucal (1334652-32-2) → 3,4-di-O-(p-methoxybenzyl)-5a-carba-D-glucal (1334652-29-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 5 h / 45 °C / Inert atmosphere

2.1: potassium hexamethylsilazane / tetrahydrofuran / 1.5 h / -78 - 0 °C / Inert atmosphere

2.2: 5 h / -78 - 20 °C / Inert atmosphere

3.1: 1,3-Dichlorobenzene / 0.33 h / 240 °C / Inert atmosphere

4.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 0.33 h / 20 °C / Inert atmosphere

4.2: Inert atmosphere

With sodium tetrahydroborate; potassium hexamethylsilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; acetonitrile; 1,3-Dichlorobenzene; 2.2: Wittig reaction / 3.1: Claisen rearrangement;

DOI:10.1002/chir.21003

upstream raw materials:

6-O-(tetrahydropyran-2-yl)-D-glucal

3,4-di-O-(p-methoxybenzyl)-D-glucal

1,5-anhydro-di-O-(p-methoxybenzyl)-2,6,7-trideoxy-D-arabinohepta-1,6-dienitol

3,4-di-O-(p-methoxybenzyl)-6-O-(2-tetrahydropyranyl)-D-glucal

Downstream raw materials:

6-O-benzyl-5a-carba-D-glucal

6-O-benzyl-3-O-(t-butyldimethylsilyl)-5a-carba-D-glucal

6-O-benzyl-3-O-(t-butyldimethylsilyl)-4-O-mesyl-5a-carba-D-glucal

6-O-benzyl-4-O-mesyl-5a-carba-D-glucal