[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

Base Information

• Chemical Name: [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
• CAS No.: 441311-05-3
• Molecular Formula: C₅₉H₇₀N₄O₉
• Molecular Weight: 979.226

Synonyms:

Chemical Property of [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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [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

There total 11 articles about [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 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:

benzyl bromide (100-39-0) → [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 (441311-05-3)

Guidance literature:

Multi-step reaction with 8 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) → [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 (441311-05-3)

Guidance literature:

Multi-step reaction with 9 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

Reference yield:

2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-D-glucopyranose → [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 (441311-05-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 92 percent / NaBH₄ / ethanol / 20 h

2.1: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / -15 °C

3.1: 72 percent / 46 h / 70 °C

4.1: CHCl₃ / 0.25 h / 20 °C

4.2: 84 percent / CHCl₃ / 24 h / 70 °C

5.1: 88 percent / NaOH / methanol / 16 h

With dmap; sodium hydroxide; sodium tetrahydroborate; triethylamine; In methanol; ethanol; dichloromethane; chloroform;

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

upstream raw materials:

2-[(2S,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylamine

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

benzyl bromide

pent-4-enyl α,β-D-glucopyranoside

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