methyl 2,3,4-tri-O-benzyl-6-deoxy-6-{[(1R,2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)cyclohexyl]amino}-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,4-tri-O-benzyl-6-deoxy-6-{[(1R,2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)cyclohexyl]amino}-α-D-glucopyranoside
CAS No.:637330-08-6
Molecular Formula:C₃₅H₄₅NO₉
Molecular Weight:623.744
Hs Code.:

Synonyms:methyl 2,3,4-tri-O-benzyl-6-deoxy-6-{[(1R,2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)cyclohexyl]amino}-α-D-glucopyranoside

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Chemical Property of methyl 2,3,4-tri-O-benzyl-6-deoxy-6-{[(1R,2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)cyclohexyl]amino}-α-D-glucopyranoside

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Technology Process of methyl 2,3,4-tri-O-benzyl-6-deoxy-6-{[(1R,2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)cyclohexyl]amino}-α-D-glucopyranoside

There total 5 articles about methyl 2,3,4-tri-O-benzyl-6-deoxy-6-{[(1R,2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)cyclohexyl]amino}-α-D-glucopyranoside 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: 100.0%

: 498539-44-9
methyl 6-{[(1'R,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside

: 637330-08-6
methyl 2,3,4-tri-O-benzyl-6-deoxy-6-{[(1R,2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)cyclohexyl]amino}-α-D-glucopyranoside

Guidance literature:: With trifluoroacetic acid; In tetrahydrofuran; water; at 20 ℃; for 40h;
DOI:10.1016/j.tet.2003.09.049

Reference yield:

: 243978-58-7
[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-hydroxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal

: 637330-08-6
methyl 2,3,4-tri-O-benzyl-6-deoxy-6-{[(1R,2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)cyclohexyl]amino}-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / imidazole / dimethylformamide / 24 h / 70 °C

2: 77 percent / N-bromosuccinimide / acetone; H₂O / 0.5 h / -25 °C

3: Ti(OiPr)4 / ethanol / 2 h / 20 °C

4: sodium cyanoborohydride / ethanol / 14 h / 20 °C

5: 100 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 40 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; N-Bromosuccinimide; sodium cyanoborohydride; trifluoroacetic acid; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tet.2003.09.049

Reference yield:

: 498539-40-5
[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tert-butyl(dimethyl)silyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one

: 637330-08-6
methyl 2,3,4-tri-O-benzyl-6-deoxy-6-{[(1R,2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)cyclohexyl]amino}-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: Ti(OiPr)4 / ethanol / 2 h / 20 °C

2: sodium cyanoborohydride / ethanol / 14 h / 20 °C

3: 100 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 40 h / 20 °C

With titanium(IV) isopropylate; sodium cyanoborohydride; trifluoroacetic acid; In tetrahydrofuran; ethanol; water;
DOI:10.1016/j.tet.2003.09.049