(S)-2-(trimethylsilyl)ethyl 2-((R)-2-(((2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanoate

Base Information

• Chemical Name: (S)-2-(trimethylsilyl)ethyl 2-((R)-2-(((2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanoate
• CAS No.: 387881-21-2
• Molecular Formula: C₃₃H₄₆N₂O₉Si
• Molecular Weight: 642.822
• Mol file: 387881-21-2.mol

Synonyms:(S)-2-(trimethylsilyl)ethyl 2-((R)-2-(((2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanoate

Chemical Property of (S)-2-(trimethylsilyl)ethyl 2-((R)-2-(((2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(trimethylsilyl)ethyl 2-((R)-2-(((2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanoate

There total 1 articles about (S)-2-(trimethylsilyl)ethyl 2-((R)-2-(((2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanoate 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: 81.0%

(S)-Alanin-(2-trimethylsilylethyl)ester (103225-23-6) + benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside (73089-68-6) → (S)-2-(trimethylsilyl)ethyl 2-((R)-2-(((2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanoate (387881-21-2)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ja0166848

Reference yield: 89.0%

(S)-2-(trimethylsilyl)ethyl 2-((R)-2-(((2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanoate (387881-21-2) → (S)-2-[(R)-2-((2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionic acid 2-trimethylsilanyl-ethyl ester (387881-22-3)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 75 ℃; for 0.5h;

DOI:10.1021/ja0166848

Reference yield: 83.0%

(S)-2-(trimethylsilyl)ethyl 2-((R)-2-(((2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanoate (387881-21-2) → C26H40N2O9Si (1456708-22-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; at 20 ℃; for 12h;

DOI:10.1002/chem.201301074

upstream raw materials:

(S)-Alanin-(2-trimethylsilylethyl)ester

benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

(S)-2-[(R)-2-((2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionic acid 2-trimethylsilanyl-ethyl ester

(S)-2-[(R)-2-((2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-hydroxy-tetrahydro-pyran-4-yloxy)-propionylamino]-propionic acid 2-trimethylsilanyl-ethyl ester

(S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester

(S)-2-{(R)-2-[(2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid