(2R,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexanal

Base Information

Chemical Name:(2R,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexanal
CAS No.:130114-48-6
Molecular Formula:C₂₁H₂₉NO₈
Molecular Weight:423.463
Hs Code.:

Synonyms:(2R,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexanal

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Chemical Property of (2R,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexanal

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Technology Process of (2R,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexanal

There total 6 articles about (2R,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexanal 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%

: 130114-47-5
(2S,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexan-1-ol

: 130114-48-6
(2R,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexanal

Guidance literature:: With oxalyl dichloride; triethylamine; In dimethyl sulfoxide;

Reference yield:

: 130114-44-2
(2S,3R,4R,5S)-5-bromo-1-<(tertbutyldimethylsilyl)oxy>-2,3:4,6-bis(isopropylidenedioxy)hexane

: 130114-48-6
(2R,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexanal

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / (n-Bu)4NF / tetrahydrofuran / 2 h / Ambient temperature

2: 65 percent / sodium azide / dimethylsulfoxide / 4 h / 120 °C

3: 81 percent / H₂ / 10percent Pd-C / methanol / 4 h

4: 93 percent / triethylamine / dioxane / 4 h / Ambient temperature

5: 1.) oxalyl chloride, dimethyl sulfoxide 2.) Et₃N / 1.) CH₂Cl₂, -78 degC, 1 h 2.) a) -78 degC, 30 min b) -78 degC -> rt

With sodium azide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dimethyl sulfoxide;
DOI:10.1021/jo00002a057

Reference yield:

: 130114-46-4
(2S,3S,4S,5R)-5-azido-2,3:4,6-bis(isopropylidenedioxy)hexan-1-ol

: 130114-48-6
(2R,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexanal

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / H₂ / 10percent Pd-C / methanol / 4 h

2: 93 percent / triethylamine / dioxane / 4 h / Ambient temperature

3: 1.) oxalyl chloride, dimethyl sulfoxide 2.) Et₃N / 1.) CH₂Cl₂, -78 degC, 1 h 2.) a) -78 degC, 30 min b) -78 degC -> rt

With oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol;
DOI:10.1021/jo00002a057