N-[(1R,2S,3R)-1-((S)-1-Azido-2-hydroxy-ethyl)-2,3,4-tris-benzyloxy-butyl]-acetamide

Base Information

Chemical Name:N-[(1R,2S,3R)-1-((S)-1-Azido-2-hydroxy-ethyl)-2,3,4-tris-benzyloxy-butyl]-acetamide
CAS No.:881894-77-5
Molecular Formula:C₂₉H₃₄N₄O₅
Molecular Weight:518.613
Hs Code.:

Synonyms:N-[(1R,2S,3R)-1-((S)-1-Azido-2-hydroxy-ethyl)-2,3,4-tris-benzyloxy-butyl]-acetamide

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Chemical Property of N-[(1R,2S,3R)-1-((S)-1-Azido-2-hydroxy-ethyl)-2,3,4-tris-benzyloxy-butyl]-acetamide

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Technology Process of N-[(1R,2S,3R)-1-((S)-1-Azido-2-hydroxy-ethyl)-2,3,4-tris-benzyloxy-butyl]-acetamide

There total 12 articles about N-[(1R,2S,3R)-1-((S)-1-Azido-2-hydroxy-ethyl)-2,3,4-tris-benzyloxy-butyl]-acetamide 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: 94.0%

: 881895-03-0
N-{(1R,2S,3R)-1-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,3,4-tris-benzyloxy-butyl}-acetamide

: 881894-77-5
N-[(1R,2S,3R)-1-((S)-1-Azido-2-hydroxy-ethyl)-2,3,4-tris-benzyloxy-butyl]-acetamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1021/ol0601996

Reference yield:

: 872593-76-5
p-tolyl 2,3-anhydro-4,6-O-benzylidene-1-thio-β-D-allopyranoside

: 881894-77-5
N-[(1R,2S,3R)-1-((S)-1-Azido-2-hydroxy-ethyl)-2,3,4-tris-benzyloxy-butyl]-acetamide

Guidance literature:: Multi-step reaction with 11 steps

1.1: 91 percent / sodium azide; ammonium chloride / dimethylsulfoxide / 6 h / 80 °C

2.1: pyridine / CH₂Cl₂

3.1: 9.12 g / sodium azide / dimethylformamide / 0.5 h / 20 °C

4.1: triphenylphosphine / tetrahydrofuran / 8 h / 65 °C

4.2: 59 percent / pyridine / 0 °C

5.1: iodine; methanol / 1 h / Heating

6.1: 2.18 g / sodium hydride / dimethylformamide / 20 °C

7.1: N-bromosuccinimide / acetone; H₂O / 20 °C

8.1: 1.25 g / sodium borohydride / methanol; H₂O / 1 h / 20 °C

9.1: 93 percent / pyridine / 20 °C

10.1: 62 percent / sodium hydride / dimethylformamide / 20 °C

11.1: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

With pyridine; methanol; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; ammonium chloride; tetrabutyl ammonium fluoride; iodine; sodium hydride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol0601996

Reference yield:

: N-((2S,3S,4R,5S,6R)-3-Azido-5-hydroxy-6-hydroxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl)-acetamide

: 881894-77-5
N-[(1R,2S,3R)-1-((S)-1-Azido-2-hydroxy-ethyl)-2,3,4-tris-benzyloxy-butyl]-acetamide

Guidance literature:: Multi-step reaction with 6 steps

1: 2.18 g / sodium hydride / dimethylformamide / 20 °C

2: N-bromosuccinimide / acetone; H₂O / 20 °C

3: 1.25 g / sodium borohydride / methanol; H₂O / 1 h / 20 °C

4: 93 percent / pyridine / 20 °C

5: 62 percent / sodium hydride / dimethylformamide / 20 °C

6: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol0601996