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

Base Information

Chemical Name: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
CAS No.:1026073-51-7
Molecular Formula:C₃₆H₄₄O₈
Molecular Weight:604.741
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 15 articles about 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 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: 81.0%

: 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

: 1026073-51-7
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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 76h;

Reference yield:

: 4841-84-3
dimethyl cis-1,2,3,6-tetrahydrophthalate

: 1026073-51-7
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

Guidance literature:: Multi-step reaction with 12 steps

1.1: sodium hydroxide; water / PLE / water / 20 °C / pH 7 / phosphate buffer; Enzymatic reaction

1.2: pH 2

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

3.1: 2-mercaptopyridine-1-oxide sodium salt; 2-methylpropan-2-thiol / dmap / tetrahydrofuran / 3.33 h / Reflux; Inert atmosphere

4.1: sodium hydroxide; water / PLE / water / 20 °C / pH 7 / phosphate buffer; Enzymatic reaction

4.2: pH 2

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

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

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

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

10.2: 0.33 h / -78 °C

11.1: bromine / dichloromethane / 1 h / 0 °C

11.2: 60 h / 20 °C / Molecular sieve

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 74 h

With oxalyl dichloride; tetrabutyl ammonium fluoride; water; bromine; 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; 3-chloro-benzenecarboperoxoic acid; potassium iodide; sodium hydroxide; dmap; PLE; N,N-dimethyl-formamide; In tetrahydrofuran; diethyl ether; dichloromethane; water;

Reference yield:

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

: 1026073-51-7
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

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium hydroxide; water / PLE / water / 20 °C / pH 7 / phosphate buffer; Enzymatic reaction

1.2: pH 2

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

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

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

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

7.2: 0.33 h / -78 °C

8.1: bromine / dichloromethane / 1 h / 0 °C

8.2: 60 h / 20 °C / Molecular sieve

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 74 h

With tetrabutyl ammonium fluoride; water; bromine; iodine; copper(l) cyanide; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; potassium iodide; sodium hydroxide; PLE; In tetrahydrofuran; diethyl ether; dichloromethane; water;