4-(3-Methoxy-4-{2-[(2S,3R,4R,5S)-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylcarbamoyloxymethyl}-phenoxy)-butyric acid

Base Information

• Chemical Name: 4-(3-Methoxy-4-{2-[(2S,3R,4R,5S)-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylcarbamoyloxymethyl}-phenoxy)-butyric acid
• CAS No.: 441310-91-4
• Molecular Formula: C₅₈H₆₈N₂O₁₀Si
• Molecular Weight: 981.271
• Mol file: 441310-91-4.mol

Synonyms:4-(3-Methoxy-4-{2-[(2S,3R,4R,5S)-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylcarbamoyloxymethyl}-phenoxy)-butyric acid

Chemical Property of 4-(3-Methoxy-4-{2-[(2S,3R,4R,5S)-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylcarbamoyloxymethyl}-phenoxy)-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(3-Methoxy-4-{2-[(2S,3R,4R,5S)-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylcarbamoyloxymethyl}-phenoxy)-butyric acid

There total 12 articles about 4-(3-Methoxy-4-{2-[(2S,3R,4R,5S)-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylcarbamoyloxymethyl}-phenoxy)-butyric acid 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: 88.0%

4-(3-Methoxy-4-{2-[(2S,3R,4R,5S)-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylcarbamoyloxymethyl}-phenoxy)-butyric acid methyl ester (441310-90-3) → 4-(3-Methoxy-4-{2-[(2S,3R,4R,5S)-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylcarbamoyloxymethyl}-phenoxy)-butyric acid (441310-91-4)

Guidance literature:

With sodium hydroxide; In methanol; for 16h;

DOI:10.1016/S0040-4039(02)00250-2

Reference yield:

benzyl bromide (100-39-0) → 4-(3-Methoxy-4-{2-[(2S,3R,4R,5S)-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylcarbamoyloxymethyl}-phenoxy)-butyric acid (441310-91-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 85 percent / NaH; 18-crown-6 / tetrahydrofuran / 19 h / 70 °C

2.1: 70 percent / NBS / acetonitrile; H₂O / 2 h

3.1: 92 percent / NaBH₄ / ethanol / 20 h

4.1: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / -15 °C

5.1: 72 percent / 46 h / 70 °C

6.1: CHCl₃ / 0.25 h / 20 °C

6.2: 84 percent / CHCl₃ / 24 h / 70 °C

7.1: 88 percent / NaOH / methanol / 16 h

With dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; 18-crown-6 ether; sodium hydride; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; acetonitrile;

DOI:10.1016/S0040-4039(02)00250-2

Reference yield:

pent-4-enyl α,β-D-glucopyranoside (182074-52-8) → 4-(3-Methoxy-4-{2-[(2S,3R,4R,5S)-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylcarbamoyloxymethyl}-phenoxy)-butyric acid (441310-91-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 94 percent / DBU / tetrahydrofuran / 22 h

2.1: 85 percent / NaH; 18-crown-6 / tetrahydrofuran / 19 h / 70 °C

3.1: 70 percent / NBS / acetonitrile; H₂O / 2 h

4.1: 92 percent / NaBH₄ / ethanol / 20 h

5.1: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / -15 °C

6.1: 72 percent / 46 h / 70 °C

7.1: CHCl₃ / 0.25 h / 20 °C

7.2: 84 percent / CHCl₃ / 24 h / 70 °C

8.1: 88 percent / NaOH / methanol / 16 h

With dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; 18-crown-6 ether; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; acetonitrile;

DOI:10.1016/S0040-4039(02)00250-2

upstream raw materials:

4-(3-Methoxy-4-{2-[(2S,3R,4R,5S)-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylcarbamoyloxymethyl}-phenoxy)-butyric acid methyl ester

benzyl bromide

pent-4-enyl α,β-D-glucopyranoside

pent-4-enyl 6-O-tert-butyldiphenylsilyl-D-glucopyranoside

Downstream raw materials:

[2-((2S,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-hydroxymethyl-piperidin-1-yl)-ethyl]-carbamic acid (2S,3R,4R,5S)-1-(2-amino-ethyl)-3,4,5-tris-benzyloxy-piperidin-2-ylmethyl ester