N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine

Base Information

• Chemical Name: N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine
• CAS No.: 301532-85-4
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347

Synonyms:N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine

Chemical Property of N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine

Chemical Property:

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Technology Process of N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine

There total 2 articles about N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine 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%

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde (33985-40-9) + benzylamine (100-46-9) → N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine (301532-85-4)

Guidance literature:

DOI:10.1016/S0040-4020(00)00410-5

Reference yield:

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (4099-85-8,828937-29-7) → N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine (301532-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / PCC / CH₂Cl₂ / 20 °C

2: 100 percent

With pyridinium chlorochromate; In dichloromethane; 1: Oxidation / 2: Condensation;

DOI:10.1016/S0040-4020(00)00410-5

Reference yield: 30.0%

Methoxyacetyl chloride (38870-89-2) + N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine (301532-85-4) → cis-1-(benzyl)-3-methoxy-4-(methyl-2,3-O-isopropylidene-β-D-ribopento-1,4-furanoside)-azetidin-2-one (301532-86-5)

Guidance literature:

With triethylamine; In dichloromethane; at -20 - 20 ℃;

DOI:10.1016/S0040-4020(00)00410-5

upstream raw materials:

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

benzylamine

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

Downstream raw materials:

cis-1-(benzyl)-3-methoxy-4-(methyl-2,3-O-isopropylidene-β-D-ribopento-1,4-furanoside)-azetidin-2-one

(3S,4R)-1-Benzyl-4-((2R,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-methoxy-azetidin-2-one

methyl 5-(benzylamino)-5-deoxy-1-O-methyl-2,3-di-O-isopropylidene-β-D-allofuranuronate

5-(benzylamino)-5-deoxy-1-O-methyl-2,3-di-O-isopropylidene-β-D-allofuranuronic acid N-carboxy anhydride

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