(1R,2R)-1-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

Base Information

Chemical Name:(1R,2R)-1-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol
CAS No.:1574347-82-2
Molecular Formula:C₃₉H₅₅NO₆Si
Molecular Weight:661.954
Hs Code.:

Synonyms:(1R,2R)-1-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,2R)-1-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

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Technology Process of (1R,2R)-1-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

There total 5 articles about (1R,2R)-1-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol 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: 79.0%

: 1574347-81-1
(1R,2R)-1-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

: 1574347-82-2
(1R,2R)-1-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

Guidance literature:: With triphenylphosphine; In tetrahydrofuran; methanol; at 60 ℃; for 3h; Inert atmosphere;
DOI:10.1039/c3ob42164c

Reference yield:

: 1574347-79-7
(1R,2R)-1-O-(2-azido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

: 1574347-82-2
(1R,2R)-1-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium methylate; methanol / dichloromethane / 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

2.2: 24 h / 20 °C / Inert atmosphere

3.1: triphenylphosphine / tetrahydrofuran; methanol / 3 h / 60 °C / Inert atmosphere

With methanol; sodium methylate; sodium hydride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1039/c3ob42164c

Reference yield:

: 1574347-72-0
(1R,2R)-1-O-(2-azido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)cyclohexanediol

: 1574347-82-2
(1R,2R)-1-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-(tert-butyldimethylsilyl)cyclohexanediol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: sodium methylate; methanol / dichloromethane / 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

3.2: 24 h / 20 °C / Inert atmosphere

4.1: triphenylphosphine / tetrahydrofuran; methanol / 3 h / 60 °C / Inert atmosphere

With 2,6-dimethylpyridine; methanol; sodium methylate; sodium hydride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1039/c3ob42164c