(E)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexo-pyranosid-4-yl)-D-gluco-hex-1-enose

Base Information

Chemical Name:(E)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexo-pyranosid-4-yl)-D-gluco-hex-1-enose
CAS No.:138459-04-8
Molecular Formula:C₅₃H₆₄O₉Si
Molecular Weight:873.171
Hs Code.:

(E)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexo-pyranosid-4-yl)-D-gluco-hex-1-enose

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexo-pyranosid-4-yl)-D-gluco-hex-1-enose

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Technology Process of (E)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexo-pyranosid-4-yl)-D-gluco-hex-1-enose

There total 18 articles about (E)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexo-pyranosid-4-yl)-D-gluco-hex-1-enose 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: 89.0%

: 138459-03-7,138514-62-2
(E)-1,2-Dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hexo-1-enose

: 58479-61-1
tert-butylchlorodiphenylsilane

: 138459-04-8,138514-63-3
(Z)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 3h;
DOI:10.1021/jo00029a024

Reference yield: 81.0%

: 138459-03-7,138514-62-2
(Z)-1,2-Dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hexo-1-enose

: 58479-61-1
tert-butylchlorodiphenylsilane

: 138459-04-8,138514-63-3
(E)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexo-pyranosid-4-yl)-D-gluco-hex-1-enose

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 8h;
DOI:10.1021/jo00029a024

Reference yield:

: 10323-20-3
D-Arabinose

: 138459-04-8,138514-63-3
(Z)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose

Guidance literature:: Multi-step reaction with 6 steps

1: 1) conc. HCl / 1) 30 min, 2) 2 h

2: 86 percent / p-TsOH / methanol; H₂O / 36 h / -10 °C

3: 89 percent / imidazole / dimethylformamide / 18 h / 25 °C

4: 97 percent / NBS, 2,6-lutidine / acetonitrile; H₂O / 0.17 h / 25 °C

6: 89 percent / imidazole / dimethylformamide / 3 h

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; N-Bromosuccinimide; toluene-4-sulfonic acid; In methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00029a024