1,6-anhydro-3-O-benzyl-4-O-(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-β-D-glucopyranose

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Chemical Name:1,6-anhydro-3-O-benzyl-4-O-(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-β-D-glucopyranose
CAS No.:110403-83-3
Molecular Formula:C₃₀H₃₇N₃O₁₀
Molecular Weight:599.638
Hs Code.:

Synonyms:1,6-anhydro-3-O-benzyl-4-O-(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-β-D-glucopyranose

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Chemical Property of 1,6-anhydro-3-O-benzyl-4-O-(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-β-D-glucopyranose

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Technology Process of 1,6-anhydro-3-O-benzyl-4-O-(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-β-D-glucopyranose

There total 16 articles about 1,6-anhydro-3-O-benzyl-4-O-(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-β-D-glucopyranose 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: 80.0%

: (2R,3S,4S,5R,6R)-5-Azido-6-[(1R,2R,3S,4R,5R)-3-benzyloxy-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

: 77-76-9
2,2-dimethoxy-propane

: 110403-83-3
1,6-anhydro-3-O-benzyl-4-O-(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-β-D-glucopyranose

Guidance literature:: With toluene-4-sulfonic acid; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)96231-2

Reference yield:

: Methanesulfonic acid (4aR,6R,7R,8S,8aR)-6-((1R,2S,3R,4R,5R)-3,4-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-7-methanesulfonyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

: 110403-83-3
1,6-anhydro-3-O-benzyl-4-O-(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) MeONa / 1.) MeOH; 2.) pyridine

2: 85 percent / Bu₄NHSO₄, 50percent aq.NaOH / toluene / -15 °C

3: 67 percent / NaOMe / methanol; CH₂Cl₂ / 0 °C

4: 87 percent / NaH, Bu₄NI

5: 39 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol / 90 °C

6: 1.) Me₂SO; 2.) NaBH₄ / 1.) Ac₂O; 2.) EtOH, O deg C

7: 80 percent / TsOH / tetrahydrofuran

With sodium hydroxide; sodium tetrahydroborate; sodium azide; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; 2-methoxy-ethanol; toluene;
DOI:10.1016/S0040-4039(00)96231-2

Reference yield:

: 114048-00-9
1,6-anhydro-3-O-benzyl-4',6'-O-benzylidene-2',3'-di-O-methylsulphonyl-2-O-pivaloyl-β-maltose

: 110403-83-3
1,6-anhydro-3-O-benzyl-4-O-(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: 67 percent / NaOMe / methanol; CH₂Cl₂ / 0 °C

2: 87 percent / NaH, Bu₄NI

3: 39 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol / 90 °C

4: 1.) Me₂SO; 2.) NaBH₄ / 1.) Ac₂O; 2.) EtOH, O deg C

5: 80 percent / TsOH / tetrahydrofuran

With sodium tetrahydroborate; sodium azide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; 2-methoxy-ethanol;
DOI:10.1016/S0040-4039(00)96231-2