Acetic acid (2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-6-chloro-5-((2R,3S,4S,5R,6R)-3,5-diacetoxy-6-acetoxymethyl-4-carbamoyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-6-chloro-5-((2R,3S,4S,5R,6R)-3,5-diacetoxy-6-acetoxymethyl-4-carbamoyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 217180-01-3
• Molecular Formula: C₃₅H₄₂ClNO₁₅
• Molecular Weight: 752.169
• Mol file: 217180-01-3.mol

Synonyms:Acetic acid (2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-6-chloro-5-((2R,3S,4S,5R,6R)-3,5-diacetoxy-6-acetoxymethyl-4-carbamoyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Acetic acid (2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-6-chloro-5-((2R,3S,4S,5R,6R)-3,5-diacetoxy-6-acetoxymethyl-4-carbamoyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-6-chloro-5-((2R,3S,4S,5R,6R)-3,5-diacetoxy-6-acetoxymethyl-4-carbamoyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

There total 1 articles about Acetic acid (2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-6-chloro-5-((2R,3S,4S,5R,6R)-3,5-diacetoxy-6-acetoxymethyl-4-carbamoyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-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: 100.0%

1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranose (102871-17-0) → Acetic acid (2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-6-chloro-5-((2R,3S,4S,5R,6R)-3,5-diacetoxy-6-acetoxymethyl-4-carbamoyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (217180-01-3)

Guidance literature:

With hydrogenchloride; In dichloromethane;

DOI:10.1021/ja9819458

Reference yield: 12.0%

L-erythro-Nα,Nim-di-tert-butoxycarbonyl-β-hydroxyhistidine benzyl ester (83044-04-6) + Acetic acid (2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-6-chloro-5-((2R,3S,4S,5R,6R)-3,5-diacetoxy-6-acetoxymethyl-4-carbamoyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (217180-01-3) → C53H64N4O20 (217180-09-1) + C58H72N4O22 (217180-08-0)

Guidance literature:

With silver trifluoromethanesulfonate; tetramethylurea; In 1,2-dichloro-ethane; at 48 ℃; for 22h;

DOI:10.1021/ja9819458

Reference yield:

Acetic acid (2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-6-chloro-5-((2R,3S,4S,5R,6R)-3,5-diacetoxy-6-acetoxymethyl-4-carbamoyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (217180-01-3) → C64H83N5O24 (217180-13-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 11 percent / AgOTf, 1,1,3,3-tetramethylurea / 1,2-dichloro-ethane / 22 h / 48 °C

2: 64 percent / pyridine / 1 h / 25 °C

3: 54 percent / H₂ / 10percent Pd/C / ethanol / 20 h / 25 °C / 760 Torr

4: 70 percent / N,N-diisopropylethylamine, 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 5 h / 25 °C

With pyridine; hydrogen; silver trifluoromethanesulfonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; tetramethylurea; palladium on activated charcoal; In ethanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ja9819458

upstream raw materials:

1,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-β-L-gulopyranose

Downstream raw materials:

C₅₃H₆₄N₄O₂₀

C₅₈H₇₂N₄O₂₂

C₆₄H₈₃N₅O₂₄

C₅₁H₆₆N₄O₂₂