2-cyano-4-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)crotononitrile

Base Information

• Chemical Name: 2-cyano-4-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)crotononitrile
• CAS No.: 594837-79-3
• Molecular Formula: C₂₆H₂₆N₂O₅
• Molecular Weight: 446.503

Synonyms:2-cyano-4-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)crotononitrile

Chemical Property of 2-cyano-4-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)crotononitrile

Chemical Property:

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Technology Process of 2-cyano-4-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)crotononitrile

There total 2 articles about 2-cyano-4-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)crotononitrile 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: 87.0%

malononitrile (109-77-3) + 2-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)ethanal (593280-25-2) → 2-cyano-4-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)crotononitrile (594837-79-3)

Guidance literature:

With aluminum oxide; In toluene; for 1h; Heating;

DOI:10.1081/CAR-120021697

Reference yield:

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-(prop-2-enyl)-α-D-altropyranoside (131529-43-6) → 2-cyano-4-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)crotononitrile (594837-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / OsO₄; NaIO₄ / dioxane; H₂O / 2 h / 20 °C

2: 87 percent / Al₂O₃ / toluene / 1 h / Heating

With aluminum oxide; sodium periodate; osmium(VIII) oxide; In 1,4-dioxane; water; toluene; 2: Knoevenagel reaction;

DOI:10.1081/CAR-120021697

Reference yield: 82.0%

2-cyano-4-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)crotononitrile (594837-79-3) → 2-amino-5-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)thiophene-3-carbonitrile (593280-27-4)

Guidance literature:

With sulfur; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1081/CAR-120021697

upstream raw materials:

malononitrile

2-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)ethanal

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-(prop-2-enyl)-α-D-altropyranoside

Downstream raw materials:

2-amino-5-(methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranosid-2-yl)thiophene-3-carbonitrile

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