1D-1,7-O-benzylidene-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

Base Information

Chemical Name:1D-1,7-O-benzylidene-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol
CAS No.:73619-36-0
Molecular Formula:C₂₉H₃₅NO₁₄
Molecular Weight:621.595
Hs Code.:

1D-1,7-O-benzylidene-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

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Chemical Property of 1D-1,7-O-benzylidene-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

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Technology Process of 1D-1,7-O-benzylidene-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

There total 15 articles about 1D-1,7-O-benzylidene-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol 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: 74.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 73619-35-9,73651-24-8
1L-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

: 73619-36-0,73651-25-9
1L-1,7-O-benzylidene-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

Guidance literature:: acid; In N,N-dimethyl-formamide;
DOI:10.1246/cl.1980.135

Reference yield: 66.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 73619-35-9,73651-24-8
1D-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

: 73619-36-0,73651-25-9
1D-1,7-O-benzylidene-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

Guidance literature:: acid; In N,N-dimethyl-formamide;
DOI:10.1246/cl.1980.135

Reference yield:

: 64589-26-0,68108-50-9,73651-28-2,74561-05-0,87038-27-5,108866-25-7,132342-13-3
(+/-)-<(1,3/2,4,5)-5-acetamido-2,3,4-triacetoxycyclohexyl>-methyl acetate

: 73619-36-0,73651-25-9
1L-1,7-O-benzylidene-3,4-N,O-carbonyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / 4M aq. hydrochloric acid / 2 h / Heating

2: 52.3 percent / aq. sodium hydroxide / acetone; toluene / 17 h / Ambient temperature

3: 75 percent / aq. sodium hydroxide / acetone / 4 h / Ambient temperature

4: 79 percent / p-toluenesulfonic acid / dimethylformamide / 2 h / 80 °C

5: 47 percent / mercury(II) cyanide, calcium sulfate / benzene; dioxane / 140 h / 65 °C

6: 44 percent / 80percent aq. acetic acid / 18 h / Ambient temperature

7: 74 percent / p-toluenesulfonic acid / dimethylformamide / 1.5 h / 60 °C

With hydrogenchloride; calcium sulfate; sodium hydroxide; mercury(II) cyanide; toluene-4-sulfonic acid; acetic acid; In 1,4-dioxane; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1246/bcsj.56.494