2,6-anhydro-2-<(benzyloxy)methyl>-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octanenitrile

Base Information

Chemical Name:2,6-anhydro-2-<(benzyloxy)methyl>-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octanenitrile
CAS No.:109150-84-7
Molecular Formula:C₂₂H₂₉NO₆
Molecular Weight:403.475
Hs Code.:

Synonyms:2,6-anhydro-2-<(benzyloxy)methyl>-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octanenitrile

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Chemical Property of 2,6-anhydro-2-<(benzyloxy)methyl>-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octanenitrile

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Technology Process of 2,6-anhydro-2-<(benzyloxy)methyl>-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octanenitrile

There total 9 articles about 2,6-anhydro-2-<(benzyloxy)methyl>-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octanenitrile 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: 79.0%

: 100-39-0
benzyl bromide

: 109150-83-6
2,6-anhydro-3-deoxy-2-(hydroxymethyl)-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octanenitrile

: 109150-84-7
2,6-anhydro-2-<(benzyloxy)methyl>-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octanenitrile

Guidance literature:: With sodium hydride; In diethyl ether; N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1021/jo00226a010

Reference yield:

: 85382-90-7
methyl-4,5,7,8-tetra-O-acetyl-2,6-anhydro-2,3-dideoxy-D-manno-oct-2-enosonat

: 109150-84-7
2,6-anhydro-2-<(benzyloxy)methyl>-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octanenitrile

Guidance literature:: Multi-step reaction with 6 steps

1: H₂ / Pd/C 10percent / ethyl acetate / 12 h / 2068.6 Torr

2: 100 percent / CH₃ONa / methanol / 1 h

3: 87 percent / p-toluenosulfonic acid, MgSO₄ / acetone / 3 h / Ambient temperature

4: 1.) LDA / 1.) THF, -75 deg C, 30 min, 2.) THF, from -75 deg C to RT

5: 91 percent / NaBH₄ / methanol / 2 h / -10 °C

6: 79 percent / NaH / dimethylformamide; diethyl ether / Ambient temperature

With sodium tetrahydroborate; hydrogen; sodium methylate; sodium hydride; magnesium sulfate; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In methanol; diethyl ether; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00226a010

Reference yield:

: 73650-00-7
methyl 4,5,7,8-tetra-O-acetyl-3-deoxyl-alpha-D-manno-2-octulopyranosonate

: 109150-84-7
2,6-anhydro-2-<(benzyloxy)methyl>-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octanenitrile

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / TiCl₄ / CH₂Cl₂ / 4 h / Ambient temperature

2: 68 percent / H₂ / Pd/C 10percent / pyridine; toluene / 8 h / 2068.6 Torr

3: 100 percent / CH₃ONa / methanol / 1 h

4: 87 percent / p-toluenosulfonic acid, MgSO₄ / acetone / 3 h / Ambient temperature

5: 1.) LDA / 1.) THF, -75 deg C, 30 min, 2.) THF, from -75 deg C to RT

6: 91 percent / NaBH₄ / methanol / 2 h / -10 °C

7: 79 percent / NaH / dimethylformamide; diethyl ether / Ambient temperature

With sodium tetrahydroborate; hydrogen; sodium methylate; titanium tetrachloride; sodium hydride; magnesium sulfate; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/jo00226a010