Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[2,5-bis-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzyloxy]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[2,5-bis-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzyloxy]-tetrahydro-pyran-4-yl ester
• CAS No.: 83476-63-5
• Molecular Formula: C₅₁H₆₆O₃₀
• Molecular Weight: 1159.07
• Mol file: 83476-63-5.mol

Synonyms:Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[2,5-bis-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzyloxy]-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[2,5-bis-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzyloxy]-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[2,5-bis-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzyloxy]-tetrahydro-pyran-4-yl ester

There total 3 articles about Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[2,5-bis-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzyloxy]-tetrahydro-pyran-4-yl 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:

per-O-acetyl-α-D-mannopyranose (4163-65-9) → Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[2,5-bis-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzyloxy]-tetrahydro-pyran-4-yl ester (83476-63-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / SnCl₄ / 1,2-dichloro-ethane / 4 h / Ambient temperature

2: dicobalt octacarbonyl / xylene / 504 h / Heating

With tin(IV) chloride; dicobalt octacarbonyl; In 1,2-dichloro-ethane; xylene;

DOI:10.1021/jo00146a023

Reference yield:

propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (83476-52-2) → Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[2,5-bis-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzyloxy]-tetrahydro-pyran-4-yl ester (83476-63-5) + Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[3,5-bis-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzyloxy]-tetrahydro-pyran-4-yl ester

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/S0040-4039(99)00674-7

Reference yield:

propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (83476-52-2) → C51H66O30 (83476-72-6) + Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[2,5-bis-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzyloxy]-tetrahydro-pyran-4-yl ester (83476-63-5)

Guidance literature:

dicobalt octacarbonyl; In xylene; for 504h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1021/jo00146a023

upstream raw materials:

propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

per-O-acetyl-α-D-mannopyranose