(1E)-2,3,5-tri-O-benzyl-4-deoxy-4-iodo-L-xylose O-[(tert-butyl)triphenylsilyl]oxime

Base Information

Chemical Name:(1E)-2,3,5-tri-O-benzyl-4-deoxy-4-iodo-L-xylose O-[(tert-butyl)triphenylsilyl]oxime
CAS No.:631915-22-5
Molecular Formula:C₄₂H₄₆INO₄Si
Molecular Weight:783.822
Hs Code.:

Synonyms:(1E)-2,3,5-tri-O-benzyl-4-deoxy-4-iodo-L-xylose O-[(tert-butyl)triphenylsilyl]oxime

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Chemical Property of (1E)-2,3,5-tri-O-benzyl-4-deoxy-4-iodo-L-xylose O-[(tert-butyl)triphenylsilyl]oxime

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Technology Process of (1E)-2,3,5-tri-O-benzyl-4-deoxy-4-iodo-L-xylose O-[(tert-butyl)triphenylsilyl]oxime

There total 6 articles about (1E)-2,3,5-tri-O-benzyl-4-deoxy-4-iodo-L-xylose O-[(tert-butyl)triphenylsilyl]oxime 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: 73.0%

: 60933-68-8
3,4,6-tri-O-benzyl-β-D-arabinofuranoside

: 58479-61-1
tert-butylchlorodiphenylsilane

: (1Z)-2,3,5-tri-O-benzyl-4-deoxy-4-iodo-L-xylose O-[(tert-butyl)triphenylsilyl]oxime

: 631915-22-5
(1E)-2,3,5-tri-O-benzyl-4-deoxy-4-iodo-L-xylose O-[(tert-butyl)triphenylsilyl]oxime

Guidance literature:: 3,4,6-tri-O-benzyl-β-D-arabinofuranoside; With methanol; hydroxylamine hydrochloride; sodium; In hexane; water; at 20 ℃; for 2h; Inert atmosphere;

tert-butylchlorodiphenylsilane; With 1H-imidazole; In dichloromethane; at 20 ℃; for 0.5h; Overall yield = 73 percent; Overall yield = 9.69 g; Further stages; Inert atmosphere;
DOI:10.1021/acs.orglett.1c01248

Reference yield: 54.0%

: 537030-20-9
(2R,3R,4R)-2,3,5-tris(benzyloxy)-4-hydroxypentanal O-(tertbutyldiphenylsilyl)oxime

: (1Z)-2,3,5-tri-O-benzyl-4-deoxy-4-iodo-L-xylose O-[(tert-butyl)triphenylsilyl]oxime

: 631915-22-5
(1E)-2,3,5-tri-O-benzyl-4-deoxy-4-iodo-L-xylose O-[(tert-butyl)triphenylsilyl]oxime

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene; for 2h; Heating;
DOI:10.1002/hlca.200390248

Reference yield:

: 620946-66-9
(E/Z)-2,3,5-tri-O-benzyl-D-arabinose-oxime

: (2R,3S,4S)-2,3,5-tris(benzyloxy)-4-iodopentanal O-(tert-butyldiphenylsilyl) oxime

: 631915-22-5
(1E)-2,3,5-tri-O-benzyl-4-deoxy-4-iodo-L-xylose O-[(tert-butyl)triphenylsilyl]oxime

Guidance literature:: Multi-step reaction with 2 steps

1: 1H-imidazole / dichloromethane / 1.5 h / 20 °C

2: 1H-imidazole; triphenylphosphine; iodine / toluene / 2.5 h / Inert atmosphere; Reflux

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; toluene;
DOI:10.1016/j.bioorg.2022.105650