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

Base Information

• Chemical Name: (Z)-(4S,5S)-5-Acetylamino-2-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-hex-2-enoic acid methyl ester
• CAS No.: 139260-91-6
• Molecular Formula: C₃₂H₃₉NO₆Si
• Molecular Weight: 561.75
• Mol file: 139260-91-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (Z)-(4S,5S)-5-Acetylamino-2-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-hex-2-enoic 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: 89.0%

(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 (139260-90-5) → (Z)-(4S,5S)-5-Acetylamino-2-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-hex-2-enoic acid methyl ester (139260-91-6)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -78 ℃;

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 → (Z)-(4S,5S)-5-Acetylamino-2-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-hex-2-enoic acid methyl ester (139260-91-6)

Guidance literature:

Multi-step reaction with 7 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

5: 92 percent / 1,3-propanedithiol, NEt₃ / methanol / Ambient temperature

6: pyridine / Ambient temperature

7: 89 percent / t-BuOK / tetrahydrofuran / -78 °C

With pyridine; 1.3-propanedithiol; sodium azide; MS 4 Angstroem; potassium tert-butylate; toluene-4-sulfonic acid; triethylamine; tetramethylurea; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

(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 (139260-87-0) → (Z)-(4S,5S)-5-Acetylamino-2-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-hex-2-enoic acid methyl ester (139260-91-6)

Guidance literature:

Multi-step reaction with 6 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

4: 92 percent / 1,3-propanedithiol, NEt₃ / methanol / Ambient temperature

5: pyridine / Ambient temperature

6: 89 percent / t-BuOK / tetrahydrofuran / -78 °C

With pyridine; 1.3-propanedithiol; sodium azide; MS 4 Angstroem; potassium tert-butylate; triethylamine; tetramethylurea; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

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

upstream 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

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)-{(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