(1R,2R,4R,6S)-2-hydroxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside

Base Information

• Chemical Name: (1R,2R,4R,6S)-2-hydroxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside
• CAS No.: 1026074-34-9
• Molecular Formula: C₃₅H₄₄O₆
• Molecular Weight: 560.731
• Mol file: 1026074-34-9.mol

Synonyms:(1R,2R,4R,6S)-2-hydroxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside

Chemical Property of (1R,2R,4R,6S)-2-hydroxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,4R,6S)-2-hydroxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside

There total 15 articles about (1R,2R,4R,6S)-2-hydroxy-4,6-dimethylcyclohexyl 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: 68.0%

(1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside (1026074-33-8) → (1R,2R,4R,6S)-2-hydroxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside (1026074-34-9)

Guidance literature:

(1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside; With water; acetic acid; In tetrahydrofuran; at 80 ℃; for 4h;

With water; sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃;

Reference yield:

methyl (1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-5-methylcyclohexane-1-carboxylate (1026073-45-9) → (1R,2R,4R,6S)-2-hydroxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside (1026074-34-9)

Guidance literature:

Multi-step reaction with 5 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

4: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / 1.5 h / 90 °C / Inert atmosphere

5: acetic acid / water / 4 h / 80 °C

With lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; 2,2'-azobis(isobutyronitrile); 1-chloro-1-(dimethylamino)-2-methyl-1-propene; tetrabutylammomium bromide; tri-n-butyl-tin hydride; acetic acid; copper(ll) bromide; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.201102884

Reference yield:

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 (1026073-50-6) → (1R,2R,4R,6S)-2-hydroxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside (1026074-34-9)

Guidance literature:

Multi-step reaction with 4 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

3: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / 1.5 h / 90 °C / Inert atmosphere

4: acetic acid / water / 4 h / 80 °C

With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); 1-chloro-1-(dimethylamino)-2-methyl-1-propene; tri-n-butyl-tin hydride; acetic acid; In tetrahydrofuran; water; 1,2-dichloro-ethane;

DOI:10.1002/chem.201102884

upstream raw materials:

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

(1R,4R,5R)-4-iodo-6-oxabicyclo[3.2.1]octane-7-one

methyl (1R,3R)-3-(tert-butyldimethylsilyloxy)cyclohex-4-ene-1-carboxylate

methyl (1R,3R,4R,5R)-3,4-epoxy-5-(tert-butyldimethylsilyloxy)cyclohexane-1-carboxylate

Downstream raw materials:

{(1R,2R,3S,5R)-2-[(2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranosyl)oxy]-3,5-dimethylcyclohex-1-yl} 2,4,6-tri-O-benzoyl-3-O-[(1S)-1-benzyloxycarbonyl-2-cyclohexylethyl]-β-D-galactopyranoside

Refernces

• 1、 -. "Glycomimetic replacements for hexoses and N-acetyl hexosamines". Page/Page column 30. . Retrieved 2008/12/06.