Acetonitrile, ((4S,5S,6S)-6-(beta-D-glucopyranosyloxy)-4,5-dihydroxy-2-cyclohexen-1-ylidene)-, (2Z)-

Base Information

• Chemical Name: Acetonitrile, ((4S,5S,6S)-6-(beta-D-glucopyranosyloxy)-4,5-dihydroxy-2-cyclohexen-1-ylidene)-, (2Z)-
• CAS No.: 72523-59-2
• Molecular Formula: C₁₄H₁₉NO₈
• Molecular Weight: 329.307
• Mol file: 72523-59-2.mol

Synonyms:72523-59-2;Acetonitrile, ((4S,5S,6S)-6-(beta-D-glucopyranosyloxy)-4,5-dihydroxy-2-cyclohexen-1-ylidene)-, (2Z)-

Chemical Property of Acetonitrile, ((4S,5S,6S)-6-(beta-D-glucopyranosyloxy)-4,5-dihydroxy-2-cyclohexen-1-ylidene)-, (2Z)-

Chemical Property:

• Vapor Pressure: 2.3E-20mmHg at 25°C
• Boiling Point: 662.4°Cat760mmHg
• Flash Point: 354.4°C
• PSA: 163.63000
• Density: 1.61g/cm³
• LogP: -3.08692
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 329.11106656
• Heavy Atom Count: 23
• Complexity: 526

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC#N)C(C(C1O)O)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=C/C(=C/C#N)/[C@@H]([C@H]([C@H]1O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of Acetonitrile, ((4S,5S,6S)-6-(beta-D-glucopyranosyloxy)-4,5-dihydroxy-2-cyclohexen-1-ylidene)-, (2Z)-

There total 11 articles about Acetonitrile, ((4S,5S,6S)-6-(beta-D-glucopyranosyloxy)-4,5-dihydroxy-2-cyclohexen-1-ylidene)-, (2Z)- 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: 93.0%

(2Z)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile (63568-00-3) → (-)-(2Z)-{(4R,5S,6S)-6-(β-D-glucopyranosyloxy)-4,5-dihydroxycyclohex-2-en-1-ylidene}acetonitrile (63492-69-3,72523-59-2)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 1h;

DOI:10.1002/hlca.200390065

Reference yield: 92.0%

hexaacetate of (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ1,α-acetonitrile (84799-67-7) → (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ1,α-acetonitrile (84799-31-5,72523-59-2)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 0.0833333h;

DOI:10.1002/hlca.200790015

Reference yield:

(2E)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile (561023-24-3) → (-)-(2Z)-{(4R,5S,6S)-6-(β-D-glucopyranosyloxy)-4,5-dihydroxycyclohex-2-en-1-ylidene}acetonitrile (63492-69-3,72523-59-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / dioxane / 0.67 h / UV-irradiation

2: 93 percent / NaOMe / methanol / 1 h / 0 °C

With sodium methylate; In 1,4-dioxane; methanol;

DOI:10.1002/hlca.200390065

upstream raw materials:

(2Z)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile

(2E)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile

hexaacetate of (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ^1,α-acetonitrile

(2E)-[(4R,5S,6S)-4,5-(cyclohexylidenedioxy)-6-hydroxycyclohex-2-en-1-ylidene]ethanenitrile

Downstream raw materials:

hexaacetate of (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ^1,α-acetonitrile

D-glucose

griffonilide