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

Base Information

• Chemical Name: 6-O-benzyl-4-O-mesyl-5a-carba-D-glucal
• CAS No.: 1334652-37-7
• Molecular Formula: C₁₅H₂₀O₅S
• Molecular Weight: 312.387
• Mol file: 1334652-37-7.mol

Synonyms:

Chemical Property of 6-O-benzyl-4-O-mesyl-5a-carba-D-glucal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-benzyl-4-O-mesyl-5a-carba-D-glucal

There total 11 articles about 6-O-benzyl-4-O-mesyl-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:

6-O-benzyl-3-O-(t-butyldimethylsilyl)-4-O-mesyl-5a-carba-D-glucal (1334652-36-6) → 6-O-benzyl-4-O-mesyl-5a-carba-D-glucal (1334652-37-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chir.21003

Reference yield:

3,4-di-O-(p-methoxybenzyl)-D-glucal (1334652-32-2) → 6-O-benzyl-4-O-mesyl-5a-carba-D-glucal (1334652-37-7)

Guidance literature:

Multi-step reaction with 9 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

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.67 h / 0 - 20 °C / Inert atmosphere

5.2: 2 h / 0 - 20 °C / Inert atmosphere

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h / 20 °C / Inert atmosphere

7.1: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 0 - 20 °C / Inert atmosphere

8.1: pyridine / dichloromethane / 12 h / 0 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; 1,3-Dichlorobenzene; 2.2: Wittig reaction / 3.1: Claisen rearrangement;

DOI:10.1002/chir.21003

Reference yield:

6-O-(tetrahydropyran-2-yl)-D-glucal (1033614-25-3) → 6-O-benzyl-4-O-mesyl-5a-carba-D-glucal (1334652-37-7)

Guidance literature:

Multi-step reaction with 11 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

7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.67 h / 0 - 20 °C / Inert atmosphere

7.2: 2 h / 0 - 20 °C / Inert atmosphere

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h / 20 °C / Inert atmosphere

9.1: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 0 - 20 °C / Inert atmosphere

10.1: pyridine / dichloromethane / 12 h / 0 °C / Inert atmosphere

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; water; potassium hexamethylsilazane; sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; paraffin oil; mineral oil; 1,3-Dichlorobenzene; 4.2: Wittig reaction / 5.1: 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)-5a-carba-D-glucal

Downstream raw materials:

(1)-3-O-[6-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)]-6-O-benzyl-5a-carba-D-glucal