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

Base Information

Chemical Name:(-)-(1E)-{(4R,5S,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile
CAS No.:350809-52-8
Molecular Formula:C₃₇H₅₉NO₁₂Si
Molecular Weight:737.96
Hs Code.:

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

Chemical Property:

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MSDS Files:: SDS file from LookChem

Useful:

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

There total 5 articles about (-)-(1E)-{(4R,5S,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-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: 58.0%

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

: 350809-51-7
(+)-(1E)-{(4R,5R,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-6-hydroxy-4-methoxycyclohex-2-en-1-yliden}acetonitrile

: 350809-52-8
(-)-(1E)-{(4R,5S,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃; for 14h;
DOI:10.1002/1522-2675(20010418)84:4<880::aid-hlca880>3.0.co;2-u DOI:10.1002/1522-2675(20010418)84:4<890::AID-HLCA890>3.0.CO;2-Q

Reference yield: 32.0%

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

: 350809-51-7
(+)-(1E)-{(4R,5R,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-6-hydroxy-4-methoxycyclohex-2-en-1-yliden}acetonitrile

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

: 350809-52-8
(-)-(1E)-{(4R,5S,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile

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

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In 1,2-dichloro-ethane; at -20 - 20 ℃; for 15h;
DOI:10.1002/1522-2675(20010418)84:4<880::aid-hlca880>3.0.co;2-u

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

: 350809-52-8
(-)-(1E)-{(4R,5S,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-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: 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

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