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

Base Information

• Chemical Name: hexaacetate of (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ^1,α-acetonitrile
• CAS No.: 84799-67-7
• Molecular Formula: C₂₆H₃₁NO₁₄
• Molecular Weight: 581.53
• Mol file: 84799-67-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 6 articles about hexaacetate of (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ^1,α-acetonitrile 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: 61.0%

(2E)-[(4R,5R,6S)-4,5-diacetoxy-6-{[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl]oxy}-cyclohex-2-en-1-ylidene]ethanenitrile (930117-58-1) → hexaacetate of (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ1,α-acetonitrile (84799-67-7)

Guidance literature:

In acetonitrile; for 0.216667h; Irradiation;

DOI:10.1002/hlca.200790015

Reference yield:

(2E/Z)-[(1S,4R,5R,6S)-5,6-(cyclohexylidenedioxy)-7-oxabicyclo[2.2.1]hept-2-ylidene]ethanenitrile → hexaacetate of (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ1,α-acetonitrile (84799-67-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 56 percent / (i-Pr)2NH; BuLi / hexane; tetrahydrofuran / 0.02 h / 4 °C

2.1: 62 percent / AgOTf₃; 4 Angstroem molecular sieves; 2,6-di(tert-butyl)-4-methylpyridine / 1,2-dichloro-ethane / 14 h / 20 °C

3.1: 82 percent / CF₃COOH / 1,2-dichloro-ethane / 12 h / 20 °C

4.1: MeONa / methanol / 1 h / 20 °C

4.2: 96 percent / 4-(dimethylamino)pyridine / 3 h / 20 °C

5.1: 61 percent / acetonitrile / 0.22 h / Irradiation

With n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; 1,2-dichloro-ethane; acetonitrile; 2.1: Koenigs-Knorr glycosidation;

DOI:10.1002/hlca.200790015

Reference yield:

(2E)-[(4R,5S,6S)-4,5-(cyclohexylidenedioxy)-6-hydroxycyclohex-2-en-1-ylidene]ethanenitrile (930117-55-8) → hexaacetate of (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ1,α-acetonitrile (84799-67-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 62 percent / AgOTf₃; 4 Angstroem molecular sieves; 2,6-di(tert-butyl)-4-methylpyridine / 1,2-dichloro-ethane / 14 h / 20 °C

2.1: 82 percent / CF₃COOH / 1,2-dichloro-ethane / 12 h / 20 °C

3.1: MeONa / methanol / 1 h / 20 °C

3.2: 96 percent / 4-(dimethylamino)pyridine / 3 h / 20 °C

4.1: 61 percent / acetonitrile / 0.22 h / Irradiation

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; trifluoroacetic acid; In methanol; 1,2-dichloro-ethane; acetonitrile; 1.1: Koenigs-Knorr glycosidation;

DOI:10.1002/hlca.200790015

upstream raw materials:

acetic anhydride

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

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

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

Downstream raw materials:

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

Refernces

• 1、 Ueda, Katsuhiro,Yasutomi, Kazuko,Mori, Iwao. "STRUCTURE OF A NEW CYANOGLUCOSIDE FROM ILEX WARBURGII LOESN.". . p. 149 - 150. Retrieved 2007/10/02.