ethyl (2R,3S,4R,5R)-5-azido-2,3-(isopropylidenedioxy)-4,6-bis(benzyloxy)hexanoate

Base Information

Chemical Name:ethyl (2R,3S,4R,5R)-5-azido-2,3-(isopropylidenedioxy)-4,6-bis(benzyloxy)hexanoate
CAS No.:1427467-89-7
Molecular Formula:C₂₅H₃₁N₃O₆
Molecular Weight:469.538
Hs Code.:

Synonyms:ethyl (2R,3S,4R,5R)-5-azido-2,3-(isopropylidenedioxy)-4,6-bis(benzyloxy)hexanoate

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Chemical Property of ethyl (2R,3S,4R,5R)-5-azido-2,3-(isopropylidenedioxy)-4,6-bis(benzyloxy)hexanoate

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Technology Process of ethyl (2R,3S,4R,5R)-5-azido-2,3-(isopropylidenedioxy)-4,6-bis(benzyloxy)hexanoate

There total 3 articles about ethyl (2R,3S,4R,5R)-5-azido-2,3-(isopropylidenedioxy)-4,6-bis(benzyloxy)hexanoate 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: 96.0%

: 1427467-87-5
ethyl (2R,3R,4R,5R)-5-azido-4,6-bis(benzyloxy)-2,3-dihydroxyhexanoate

: 77-76-9
2,2-dimethoxy-propane

: 1427467-89-7
ethyl (2R,3S,4R,5R)-5-azido-2,3-(isopropylidenedioxy)-4,6-bis(benzyloxy)hexanoate

Guidance literature:: With toluene-4-sulfonic acid; In acetone; at 20 ℃;
DOI:10.3998/ark.5550190.0013.925

Reference yield:

: 1427467-83-1
(2R,3R,4R)-4-azido-3,5-bis(benzyloxy)pentane-1,2-diol

: 1427467-89-7
ethyl (2R,3S,4R,5R)-5-azido-2,3-(isopropylidenedioxy)-4,6-bis(benzyloxy)hexanoate

Guidance literature:: Multi-step reaction with 4 steps

1: sodium periodate / water; acetonitrile / 0.67 h / 20 °C

2: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 °C / Inert atmosphere

3: methanesulfonamide / water; tert-butyl alcohol / 120 h / 0 °C

4: toluene-4-sulfonic acid / acetone / 20 °C

With sodium periodate; methanesulfonamide; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; lithium chloride; In water; acetone; acetonitrile; tert-butyl alcohol; 2: |Wittig Olefination / 3: |Sharpless Dihydroxylation;
DOI:10.3998/ark.5550190.0013.925

Reference yield:

: 1427467-84-2
C₁₈H₁₉N₃O₃

: 1427467-89-7
ethyl (2R,3S,4R,5R)-5-azido-2,3-(isopropylidenedioxy)-4,6-bis(benzyloxy)hexanoate

Guidance literature:: Multi-step reaction with 3 steps

1: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 °C / Inert atmosphere

2: methanesulfonamide / water; tert-butyl alcohol / 120 h / 0 °C

3: toluene-4-sulfonic acid / acetone / 20 °C

With methanesulfonamide; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; lithium chloride; In water; acetone; acetonitrile; tert-butyl alcohol; 1: |Wittig Olefination / 2: |Sharpless Dihydroxylation;
DOI:10.3998/ark.5550190.0013.925