Methyl 4,6-O-benzylidene-2-(dicyanomethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside

Base Information

• Chemical Name: Methyl 4,6-O-benzylidene-2-(dicyanomethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside
• CAS No.: 164928-23-8
• Molecular Formula: C₁₇H₁₆N₂O₄
• Molecular Weight: 312.325

Synonyms:Methyl 4,6-O-benzylidene-2-(dicyanomethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside

Chemical Property of Methyl 4,6-O-benzylidene-2-(dicyanomethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside

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Technology Process of Methyl 4,6-O-benzylidene-2-(dicyanomethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside

There total 1 articles about Methyl 4,6-O-benzylidene-2-(dicyanomethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside 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: 82.0%

methyl 4,6-O-(phenylmethylene)-3-deoxy-α-D-erythro-hexopyranoside-2-ulose (74524-02-0) + malononitrile (109-77-3) → Methyl 4,6-O-benzylidene-2-(dicyanomethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside (164928-23-8)

Guidance literature:

With aluminum oxide; In dichloromethane; for 1.5h; Ambient temperature;

Reference yield: 69.0%

Methyl 4,6-O-benzylidene-2-(dicyanomethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside (164928-23-8) → (2R,4aR,6S,9bR)-8-amino-4,4a,6,9b-tetrahydro-6-methoxy-2-phenylthieno[2',3':4,5]pyrano[3,2-d][1,3]dioxine-7-carbonitrile (887480-51-5)

Guidance literature:

With sulfur; diethylamine; In methanol; at 45 ℃; for 2h;

DOI:10.1080/07328300500495852

Reference yield: 62.0%

phenyl isothiocyanate (103-72-0) + Methyl 4,6-O-benzylidene-2-(dicyanomethylene)-2,3-dideoxy-α-D-erythro-hexopyranoside (164928-23-8) → (2R,4aR,6S,10bS)-8-amino-4a,6,10,10b-tetrahydro-6-methoxy-2-phenyl-10-phenylimino-4H-thiopyrano[3',4':4,5]pyrano[3,2-d][1,3]dioxine-7-carbonitrile

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1080/07328300500495852

upstream raw materials:

methyl 4,6-O-(phenylmethylene)-3-deoxy-α-D-erythro-hexopyranoside-2-ulose

malononitrile

Downstream raw materials:

(2R,4aR,6S,9bR)-8-amino-4,4a,6,9b-tetrahydro-6-methoxy-2-phenylthieno[2',3':4,5]pyrano[3,2-d][1,3]dioxine-7-carbonitrile

(2R,4aR,6S,9bR)-8-(aminomethylenamino)-4,4a,6,9b-tetrahydro-6-methoxy-2-phenylthieno[2',3':4,5]pyrano[3,2-d][1,3]dioxine-7-carbonitrile

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