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

Base Information

• Chemical Name: (1)-3-O-[6-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)]-6-O-benzyl-5a-carba-D-glucal
• CAS No.: 1334652-38-8
• Molecular Formula: C₂₆H₃₆O₈
• Molecular Weight: 476.567

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (1)-3-O-[6-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)]-6-O-benzyl-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-(tetrahydropyran-2-yl)-D-glucal (1033614-25-3) → (1)-3-O-[6-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)]-6-O-benzyl-5a-carba-D-glucal (1334652-38-8)

Guidance literature:

Multi-step reaction with 13 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

12.1: potassium tert-butylate / benzene / 4 h / 20 °C / Inert atmosphere

13.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; sodium tetrahydroborate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; potassium hexamethylsilazane; sodium hydride; toluene-4-sulfonic acid; 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; benzene; 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) → (1)-3-O-[6-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)]-6-O-benzyl-5a-carba-D-glucal (1334652-38-8)

Guidance literature:

Multi-step reaction with 11 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

10.1: potassium tert-butylate / benzene / 4 h / 20 °C / Inert atmosphere

11.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; sodium tetrahydroborate; potassium tert-butylate; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; toluene-4-sulfonic 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; mineral oil; 1,3-Dichlorobenzene; benzene; 2.2: Wittig reaction / 3.1: Claisen rearrangement;

DOI:10.1002/chir.21003

Reference yield:

3,4-di-O-(p-methoxybenzyl)-5a-carba-D-glucal (1334652-29-7) → (1)-3-O-[6-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)]-6-O-benzyl-5a-carba-D-glucal (1334652-38-8)

Guidance literature:

Multi-step reaction with 7 steps

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

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

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h / 20 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 0 - 20 °C / Inert atmosphere

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

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

6.1: potassium tert-butylate / benzene / 4 h / 20 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; benzene;

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

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