(1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4-chloromethyl-6-methylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside

Base Information

Chemical Name:(1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4-chloromethyl-6-methylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside
CAS No.:1026074-32-7
Molecular Formula:C₄₁H₅₇ClO₆Si
Molecular Weight:709.438
Hs Code.:

Synonyms:(1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4-chloromethyl-6-methylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside

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Chemical Property of (1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4-chloromethyl-6-methylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside

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Technology Process of (1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4-chloromethyl-6-methylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside

There total 14 articles about (1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4-chloromethyl-6-methylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside 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: 85.0%

: 1026074-30-5
(1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4-hydroxymethyl-6-methylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside

: 1026074-32-7
(1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4-chloromethyl-6-methylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside

Guidance literature:: With 1-chloro-1-(dimethylamino)-2-methyl-1-propene; In 1,2-dichloro-ethane; at 20 ℃; for 0.75h;

Reference yield:

: 1026073-45-9
methyl (1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-5-methylcyclohexane-1-carboxylate

: 1026074-32-7
(1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4-chloromethyl-6-methylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 2,6-di-tert-butyl-4-methylpyridine; tetrabutylammomium bromide; copper(ll) bromide / dichloromethane; N,N-dimethyl-formamide / 20 h / 20 °C / Molecular sieve; Inert atmosphere

2: lithium aluminium tetrahydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere

3: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / 1,2-dichloro-ethane / 0.75 h / 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; tetrabutylammomium bromide; copper(ll) bromide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.201102884

Reference yield:

: 1026073-50-6
methyl (1R,3R,4R,5S)-4-O-(2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranosyl)-3-O-(tert-butyldimethylsilyl)-3,4-dihydroxy-5-methylcyclohexane-1-carboxylate

: 1026074-32-7
(1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4-chloromethyl-6-methylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere

2: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / 1,2-dichloro-ethane / 0.75 h / 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; In tetrahydrofuran; 1,2-dichloro-ethane;
DOI:10.1002/chem.201102884