{[(3R,4S,5Z)-4-(benzyloxy)-6-iodo-3-[(p-methoxybenzyl)oxy]-4-{[(p-methoxybenzyl)oxy]methyl}-5-hexenyl]oxy}-tert-butyldimethylsilane

Base Information

Chemical Name:{[(3R,4S,5Z)-4-(benzyloxy)-6-iodo-3-[(p-methoxybenzyl)oxy]-4-{[(p-methoxybenzyl)oxy]methyl}-5-hexenyl]oxy}-tert-butyldimethylsilane
CAS No.:213912-82-4
Molecular Formula:C₃₆H₄₉IO₆Si
Molecular Weight:732.771
Hs Code.:

Synonyms:{[(3R,4S,5Z)-4-(benzyloxy)-6-iodo-3-[(p-methoxybenzyl)oxy]-4-{[(p-methoxybenzyl)oxy]methyl}-5-hexenyl]oxy}-tert-butyldimethylsilane

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Chemical Property of {[(3R,4S,5Z)-4-(benzyloxy)-6-iodo-3-[(p-methoxybenzyl)oxy]-4-{[(p-methoxybenzyl)oxy]methyl}-5-hexenyl]oxy}-tert-butyldimethylsilane

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Technology Process of {[(3R,4S,5Z)-4-(benzyloxy)-6-iodo-3-[(p-methoxybenzyl)oxy]-4-{[(p-methoxybenzyl)oxy]methyl}-5-hexenyl]oxy}-tert-butyldimethylsilane

There total 8 articles about {[(3R,4S,5Z)-4-(benzyloxy)-6-iodo-3-[(p-methoxybenzyl)oxy]-4-{[(p-methoxybenzyl)oxy]methyl}-5-hexenyl]oxy}-tert-butyldimethylsilane 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: 85.0%

: 3020-28-8
(iodomethyl)triphenylphosphonium iodide

: 228122-18-7
(2S,3R)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pentanal

: 213912-82-4
{[(3R,4S,5Z)-4-(benzyloxy)-6-iodo-3-[(p-methoxybenzyl)oxy]-4-{[(p-methoxybenzyl)oxy]methyl}-5-hexenyl]oxy}-tert-butyldimethylsilane

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2

Reference yield: 85.0%

: 29949-93-7
iodomethylenetriphenylphosphorane

: 228122-18-7
(2S,3R)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pentanal

: 213912-82-4
{[(3R,4S,5Z)-4-(benzyloxy)-6-iodo-3-[(p-methoxybenzyl)oxy]-4-{[(p-methoxybenzyl)oxy]methyl}-5-hexenyl]oxy}-tert-butyldimethylsilane

Guidance literature:: DOI:10.1016/S0040-4039(99)00546-8

Reference yield:

: 217819-76-6
(2S,3R)-2-(benzyloxy)-3-<(p-methoxybenzyl)oxy>-2-<<(p-methoxybenzyl)oxy>methyl>-4-pentenal

: 213912-82-4
{[(3R,4S,5Z)-4-(benzyloxy)-6-iodo-3-[(p-methoxybenzyl)oxy]-4-{[(p-methoxybenzyl)oxy]methyl}-5-hexenyl]oxy}-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 7 steps

1: LiAlH₄ / diethyl ether / 0.5 h

2: 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h

3: 96 percent / 9-BBN; NaOH; H₂O₂ / tetrahydrofuran; H₂O / 15 h

4: imidazole / dimethylformamide / 1 h

5: DIBAH-L / CH₂Cl₂; hexane / 1 h / -78 °C

6: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

7: 85 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; dmap; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1: Reduction / 2: Acylation / 3: hydroboration / 4: Etherification / 5: Reduction / 6: Oxidation / 7: Wittig condensation;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2