(-)-(1Z)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile

Base Information

Chemical Name:(-)-(1Z)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile
CAS No.:352426-54-1
Molecular Formula:C₃₁H₄₅NO₁₂
Molecular Weight:623.698
Hs Code.:

Synonyms:(-)-(1Z)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile

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Chemical Property of (-)-(1Z)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (-)-(1Z)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile

There total 6 articles about (-)-(1Z)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}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: 23.0%

: 352426-53-0
(+)-(1E)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile

: 352426-54-1
(-)-(1Z)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile

Guidance literature:: In 1,4-dioxane; for 0.166667h; Irradiation;
DOI:10.1002/1522-2675(20010418)84:4<890::AID-HLCA890>3.0.CO;2-Q

Reference yield:

: (2E,Z)-{(1S,4R,5R,6R)-6-endo-{[(tert-butyl)dimethylsilyl]oxy}-5-exo-methoxy-7-oxabicyclo[2.2.1]hept-2-yliden}acetonitrile

: 352426-54-1
(-)-(1Z)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile

Guidance literature:: Multi-step reaction with 5 steps

1: 36 percent / (Me₃Si)2NLi / tetrahydrofuran / 0.33 h / 0 °C

2: 27 percent / dioxane / 0.17 h / Irradiation

3: 58 percent / AgOTf; 4 Angstroem molecular sieves; 2,6-di(tert-butyl)-4-methylpyridine / 1,2-dichloro-ethane / 14 h / 20 °C

4: 95 percent / HF / acetonitrile; H₂O / 4 h / 20 °C

5: 23 percent / dioxane / 0.17 h / Irradiation

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; hydrogen fluoride; silver trifluoromethanesulfonate; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; water; 1,2-dichloro-ethane; acetonitrile; 3: Koenigs-Knorr reaction;
DOI:10.1002/1522-2675(20010418)84:4<890::AID-HLCA890>3.0.CO;2-Q

Reference yield:

: 119607-30-6
(+)-2,3,4,6-tetra-O-isobutyryl-α-D-glucopyranosyl bromide

: 352426-54-1
(-)-(1Z)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile

Guidance literature:: Multi-step reaction with 3 steps

1: 58 percent / AgOTf; 4 Angstroem molecular sieves; 2,6-di(tert-butyl)-4-methylpyridine / 1,2-dichloro-ethane / 14 h / 20 °C

2: 95 percent / HF / acetonitrile; H₂O / 4 h / 20 °C

3: 23 percent / dioxane / 0.17 h / Irradiation

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; hydrogen fluoride; silver trifluoromethanesulfonate; In 1,4-dioxane; water; 1,2-dichloro-ethane; acetonitrile; 1: Koenigs-Knorr reaction;
DOI:10.1002/1522-2675(20010418)84:4<890::AID-HLCA890>3.0.CO;2-Q