(3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-1-cyclohexene-1-carbonitrile

Base Information

• Chemical Name: (3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-1-cyclohexene-1-carbonitrile
• CAS No.: 1227264-37-0
• Molecular Formula: C₇H₉NO₄
• Molecular Weight: 171.153
• Mol file: 1227264-37-0.mol

Synonyms:(3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-1-cyclohexene-1-carbonitrile

Chemical Property of (3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-1-cyclohexene-1-carbonitrile

Chemical Property:

Purity/Quality:

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Technology Process of (3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-1-cyclohexene-1-carbonitrile

There total 1 articles about (3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-1-cyclohexene-1-carbonitrile 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: 54.0%

(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarbonitrile (138769-96-7) → (3R,4R,5R,6R)-3,4,5,6-tetrahydroxy-1-cyclohexene-1-carbonitrile + (3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-1-cyclohexene-1-carbonitrile (1227264-37-0)

Guidance literature:

With osmium(VIII) oxide; trimethylamine-N-oxide; water; In dichloromethane; at 20 ℃; for 48h; optical yield given as %de;

DOI:10.1021/ol100525r

Reference yield:

(3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-1-cyclohexene-1-carbonitrile (1227264-37-0) + t-butyldimethylsiyl triflate (69739-34-0) → (3S,4S,5R,6R)-3,4,5-tri{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-6-hydroxycyclohexene-1-carbonitrile (1227264-38-1)

Guidance literature:

With 2,6-dimethylpyridine; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol100525r

upstream raw materials:

(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarbonitrile

Downstream raw materials:

(3S,4S,5R,6R)-3,4,5-tri{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-6-hydroxycyclohexene-1-carbonitrile