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

Base Information

• Chemical Name: 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
• CAS No.: 1026073-50-6
• Molecular Formula: C₄₂H₅₈O₈Si
• Molecular Weight: 719.003

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 8 articles about 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 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: 76.0%

methyl (1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-5-methylcyclohexane-1-carboxylate (1026073-45-9) + ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside (169532-17-6,116391-11-8) → 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)

Guidance literature:

methyl (1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-5-methylcyclohexane-1-carboxylate; ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside; With 2,6-di-tert-butyl-4-methylpyridine; tetrabutylammomium bromide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 4h; Molecular sieve;

With copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 20h;

Reference yield:

(R)-(+)-methyl 3-cyclohexene-1-carboxylate (6493-77-2,49543-03-5,68000-21-5,68000-20-4) → 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)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pig liver esterase; sodium hydroxide / water / 11 h / 20 °C / pH 7 / aq. phosphate buffer

2.1: iodine; sodium hydrogencarbonate; potassium iodide / water / 24 h / 0 - 20 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 h / Reflux

4.1: sodium hydrogencarbonate / 12 h / 20 °C / Inert atmosphere

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 12 h / 20 °C

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 17 h / 10 - 20 °C

7.1: copper(l) cyanide / tetrahydrofuran; diethyl ether / 0.5 h / -78 - -10 °C / Inert atmosphere

7.2: 0.33 h / -78 °C / Inert atmosphere

7.3: 5 h / -78 °C / Inert atmosphere

8.1: 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

With 2,6-di-tert-butyl-4-methylpyridine; pig liver esterase; tetrabutylammomium bromide; iodine; copper(l) cyanide; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; potassium iodide; sodium hydroxide; copper(ll) bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/chem.201102884

Reference yield:

dimethyl cis-1,2,3,6-tetrahydrophthalate (4841-84-3) → 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)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pig liver esterase; sodium hydroxide / water / 56.5 h / 20 °C / pH 7 / aq. phosphate buffer

2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C

3.1: dmap; 2-mercaptopyridine-1-oxide sodium salt; 2-methylpropan-2-thiol / tetrahydrofuran / 3 h / Reflux

4.1: pig liver esterase; sodium hydroxide / water / 11 h / 20 °C / pH 7 / aq. phosphate buffer

5.1: iodine; sodium hydrogencarbonate; potassium iodide / water / 24 h / 0 - 20 °C / Inert atmosphere

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 h / Reflux

7.1: sodium hydrogencarbonate / 12 h / 20 °C / Inert atmosphere

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 12 h / 20 °C

9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 17 h / 10 - 20 °C

10.1: copper(l) cyanide / tetrahydrofuran; diethyl ether / 0.5 h / -78 - -10 °C / Inert atmosphere

10.2: 0.33 h / -78 °C / Inert atmosphere

10.3: 5 h / -78 °C / Inert atmosphere

11.1: 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

With dmap; 2,6-di-tert-butyl-4-methylpyridine; pig liver esterase; oxalyl dichloride; tetrabutylammomium bromide; iodine; 2-mercaptopyridine-1-oxide sodium salt; copper(l) cyanide; sodium hydrogencarbonate; 2-methylpropan-2-thiol; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; potassium iodide; sodium hydroxide; copper(ll) bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 3.1: Barton decarboxylation;

DOI:10.1002/chem.201102884

upstream raw materials:

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

ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside

dimethyl cis-1,2,3,6-tetrahydrophthalate

(R)-(+)-methyl 3-cyclohexene-1-carboxylate

Downstream raw materials:

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

methyl (1R,3R,4R,5S)-4-O-(2,3,4-tris-O-benzyl-6-deoxy-α-L-galactopyranosyl)-3,4-dihydroxy-5-methylcyclohexane-1-carboxylate

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

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

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