(2S,3S,4R,5R)-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexan-1-ol

Base Information

Chemical Name:(2S,3S,4R,5R)-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexan-1-ol
CAS No.:108818-09-3
Molecular Formula:C₂₂H₃₅NO₁₀
Molecular Weight:473.521
Hs Code.:

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

Synonyms:(2S,3S,4R,5R)-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexan-1-ol

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Chemical Property of (2S,3S,4R,5R)-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexan-1-ol

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Technology Process of (2S,3S,4R,5R)-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexan-1-ol

There total 10 articles about (2S,3S,4R,5R)-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexan-1-ol 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: 98.0%

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

: 108818-09-3
(2S,3S,4R,5R)-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexan-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h;
DOI:10.1021/jo00391a031

Reference yield:

: 50622-09-8
2,3-O-isopropylidene-L-threitol

: 108818-09-3
(2S,3S,4R,5R)-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexan-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) NaH / 1.) DME, 5 min, 2.) DME, RT, 3.5 h

2: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 deg to RT

3: 1.) NaH / 1.) benzene, RT, 1 h, 2.) benzene, RT, 1 h

4: 81 percent / DIBAL / CH₂Cl₂; toluene / 14 h / Ambient temperature

5: 1.) 4A molecular sieves, titanium(IV) isopropoxide, diethyl L-tartrate 2.) tert-butyl hydroperoxide / 1.) CH₂Cl₂, 2.) CH₂Cl₂, -20 deg C, 14 h

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

7: 91 percent / N,N-diisopropylethylamine / CHCl₃ / 3 h / Heating

8: 86 percent / H₂ / 10percent Pd on C / methanol / 4 h / 760 Torr

9: 91 percent / Et₃N / dioxane / 6 h / Ambient temperature

10: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium azide; oxalyl dichloride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; ammonium chloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; chloroform; 2-methoxy-ethanol; water; toluene;
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

: 108818-09-3
(2S,3S,4R,5R)-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexan-1-ol

Guidance literature:: Multi-step reaction with 5 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

5: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h

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