N-{(1R,2S,3R)-1-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,4-bis-benzyloxy-3-hydroxy-butyl}-acetamide

Base Information

Chemical Name:N-{(1R,2S,3R)-1-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,4-bis-benzyloxy-3-hydroxy-butyl}-acetamide
CAS No.:881895-02-9
Molecular Formula:C₃₈H₄₆N₄O₅Si
Molecular Weight:666.893
Hs Code.:

Synonyms:N-{(1R,2S,3R)-1-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,4-bis-benzyloxy-3-hydroxy-butyl}-acetamide

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Chemical Property of N-{(1R,2S,3R)-1-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,4-bis-benzyloxy-3-hydroxy-butyl}-acetamide

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Technology Process of N-{(1R,2S,3R)-1-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,4-bis-benzyloxy-3-hydroxy-butyl}-acetamide

There total 10 articles about N-{(1R,2S,3R)-1-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,4-bis-benzyloxy-3-hydroxy-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: 93.0%

: 881895-01-8
N-[(1R,2S,3R)-1-((S)-1-Azido-2-hydroxy-ethyl)-2,4-bis-benzyloxy-3-hydroxy-butyl]-acetamide

: 58479-61-1
tert-butylchlorodiphenylsilane

: 881895-02-9
N-{(1R,2S,3R)-1-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,4-bis-benzyloxy-3-hydroxy-butyl}-acetamide

Guidance literature:: With pyridine; at 20 ℃;
DOI:10.1021/ol0601996

Reference yield:

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

: 881895-02-9
N-{(1R,2S,3R)-1-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,4-bis-benzyloxy-3-hydroxy-butyl}-acetamide

Guidance literature:: Multi-step reaction with 9 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

With pyridine; methanol; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; ammonium chloride; 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

: 881895-02-9
N-{(1R,2S,3R)-1-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,4-bis-benzyloxy-3-hydroxy-butyl}-acetamide

Guidance literature:: Multi-step reaction with 4 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

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