(2S,3S,4R,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexane

Base Information

Chemical Name:(2S,3S,4R,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexane
CAS No.:108818-08-2
Molecular Formula:C₂₈H₄₉NO₁₀Si
Molecular Weight:587.783
Hs Code.:

(2S,3S,4R,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)-5-<<<p-(methoxybenzyl)oxy>carbonyl>amino>-4,6-bis(methoxymethoxy)hexane

Synonyms:(2S,3S,4R,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexane

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Chemical Property of (2S,3S,4R,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexane

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Technology Process of (2S,3S,4R,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexane

There total 10 articles about (2S,3S,4R,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexane 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: 91.0%

: 108818-07-1
(2S,3S,4R,5R)-5-amino-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexane

: 41840-29-3
p-methoxybenzyl-S-(4,6-dimethylpyrimidin-2-yl)-thiocarbonate

: 108818-08-2
(2S,3S,4R,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexane

Guidance literature:: With triethylamine; In 1,4-dioxane; for 6h; Ambient temperature;
DOI:10.1021/jo00391a031

Reference yield:

: 108818-00-4
(E)-(4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-4,5-O-(1-methylethylidene)-2-hexen-1-ol

: 108818-08-2
(2S,3S,4R,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexane

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) 4A molecular sieves, titanium(IV) isopropoxide, diethyl L-tartrate 2.) tert-butyl hydroperoxide / 1.) CH₂Cl₂, 2.) CH₂Cl₂, -20 deg C, 14 h

2: 47 percent / sodium azide, NH₄Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H₂O / 6 h / Heating

3: 91 percent / N,N-diisopropylethylamine / CHCl₃ / 3 h / Heating

4: 86 percent / H₂ / 10percent Pd on C / methanol / 4 h / 760 Torr

5: 91 percent / Et₃N / dioxane / 6 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium azide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; hydrogen; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; chloroform; 2-methoxy-ethanol; water;
DOI:10.1021/jo00391a031

Reference yield:

: 108818-01-5
(2S,3R,4S,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol

: 108818-08-2
(2S,3S,4R,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexane

Guidance literature:: Multi-step reaction with 4 steps

1: 47 percent / sodium azide, NH₄Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H₂O / 6 h / Heating

2: 91 percent / N,N-diisopropylethylamine / CHCl₃ / 3 h / Heating

3: 86 percent / H₂ / 10percent Pd on C / methanol / 4 h / 760 Torr

4: 91 percent / Et₃N / dioxane / 6 h / Ambient temperature

With sodium azide; hydrogen; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; chloroform; 2-methoxy-ethanol; water;
DOI:10.1021/jo00391a031