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

Base Information

Chemical Name:(+)-(2E)-{(4R,5S,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-(methoxymethoxy)-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile
CAS No.:558461-45-3
Molecular Formula:C₃₈H₆₁NO₁₃Si
Molecular Weight:767.987
Hs Code.:

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

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

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Chemical Property of (+)-(2E)-{(4R,5S,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-(methoxymethoxy)-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile

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

There total 2 articles about (+)-(2E)-{(4R,5S,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-(methoxymethoxy)-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}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: 72.0%

: (2E)-{(4RS,5RS,6SR)-5-{[(tert-butyl)dimethylsilyl]oxy}-6-hydroxy-4-(methoxymethoxy)cyclohex-2-en-1-ylidene}acetonitrile

: (2S,3R,4S,5R,6R)-2-bromo-6-((isobutyryloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2-methylpropanoate)

: 558461-45-3
(+)-(2E)-{(4R,5S,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-(methoxymethoxy)-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile

Guidance literature:: With 2,4-di(tert-butyl)-4-methylpyridine; silver trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃; for 14h;
DOI:10.1002/hlca.200390065

Reference yield:

: {(1SR,4RS,5RS,6RS)-6-endo-{[(tert-butyl)dimethylsilyl]oxy}-5-exo-(methoxymethoxy)-7-oxabicyclo[2.2.1]hept-2-ylidene}acetonitrile

: 558461-45-3
(+)-(2E)-{(4R,5S,6S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-(methoxymethoxy)-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: Me₃SiOTf; (Me₃Si)2NLi / tetrahydrofuran / 0.11 h / -5 °C

2: 72 percent / AgOTf; 2,4-di(tert-butyl)-4-methylpyridine / 1,2-dichloro-ethane / 14 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 2,4-di(tert-butyl)-4-methylpyridine; silver trifluoromethanesulfonate; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dichloro-ethane;
DOI:10.1002/hlca.200390065