(R)-{(4S,5R)-5-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-benzyloxy-acetic acid methyl ester

Base Information

• Chemical Name: (R)-{(4S,5R)-5-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-benzyloxy-acetic acid methyl ester
• CAS No.: 139260-89-2
• Molecular Formula: C₃₃H₄₁N₃O₆Si
• Molecular Weight: 603.791
• Mol file: 139260-89-2.mol

Synonyms:(R)-{(4S,5R)-5-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-benzyloxy-acetic acid methyl ester

Chemical Property of (R)-{(4S,5R)-5-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-benzyloxy-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-{(4S,5R)-5-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-benzyloxy-acetic acid methyl ester

There total 7 articles about (R)-{(4S,5R)-5-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-benzyloxy-acetic acid methyl ester 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:

(R)-Benzyloxy-{(4S,5S)-5-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-trifluoromethanesulfonyloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acetic acid methyl ester → (R)-{(4S,5R)-5-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-benzyloxy-acetic acid methyl ester (139260-89-2)

Guidance literature:

With sodium azide; tetramethylurea; In N,N-dimethyl-formamide; Yield given; Ambient temperature;

DOI:10.1016/0040-4039(91)85030-9

Reference yield:

benzyl bromide (100-39-0) → (R)-{(4S,5R)-5-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-benzyloxy-acetic acid methyl ester (139260-89-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / Ag₂O, MS 4 Angstroem / CH₂Cl₂ / Ambient temperature

2: pyridine / CH₂Cl₂ / -30 °C

3: NaN₃, N,N,N',N'-tetramethylurea / dimethylformamide / Ambient temperature

With pyridine; sodium azide; MS 4 Angstroem; tetramethylurea; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(91)85030-9

Reference yield:

(3R,4S,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-one → (R)-{(4S,5R)-5-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-benzyloxy-acetic acid methyl ester (139260-89-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / p-TsOH*H₂O / Ambient temperature

2: 84 percent / Ag₂O, MS 4 Angstroem / CH₂Cl₂ / Ambient temperature

3: pyridine / CH₂Cl₂ / -30 °C

4: NaN₃, N,N,N',N'-tetramethylurea / dimethylformamide / Ambient temperature

With pyridine; sodium azide; MS 4 Angstroem; toluene-4-sulfonic acid; tetramethylurea; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(91)85030-9

upstream raw materials:

benzyl bromide

(R)-{(4R,5R)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hydroxy-acetic acid methyl ester

(R)-Benzyloxy-{(4S,5R)-5-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acetic acid methyl ester

tert-butylchlorodiphenylsilane

Downstream raw materials:

(R)-{(4S,5R)-5-[(S)-1-Acetylamino-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-benzyloxy-acetic acid methyl ester

(Z)-(4S,5S)-5-Acetylamino-2-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-hex-2-enoic acid methyl ester