Acetic acid (3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 67772-73-0
• Molecular Formula: C₂₈H₃₈O₁₉
• Molecular Weight: 678.598
• Mol file: 67772-73-0.mol

Synonyms:

Chemical Property of Acetic acid (3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

There total 11 articles about Acetic acid (3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-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: 83.0%

trimethylsilyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (19126-95-5) + hexanal (66-25-1) → 2,4,6-tri-n-pentyl-1,3,5-trioxane (7510-30-7) + Acetic acid (3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (22554-66-1,22554-67-2,25018-27-3,28140-36-5,55676-46-5,58691-31-9,58691-32-0,67772-73-0,74080-42-5,84049-75-2,97058-18-9,103475-61-2) + Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexyloxy]-tetrahydro-pyran-3-yl ester (133851-55-5)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 72h; Product distribution; other aldehydes; product yield depends on educt ratio and space requirement of aldehyde;

Reference yield: 37.0%

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) → Octa-O-acetyl-β-D-glucopyranosyl-β-D-glucopyranose (22554-66-1,22554-67-2,25018-27-3,28140-36-5,55676-46-5,58691-31-9,58691-32-0,67772-73-0,74080-42-5,84049-75-2,97058-18-9,103475-61-2)

Guidance literature:

With boron trifluoride diethyl etherate; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at 0 ℃; Molecular sieve;

DOI:10.1002/ejoc.201601439

Reference yield: 16.0%

trimethylsilyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (19126-95-5) + acetone (67-64-1) → isopropenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (114828-10-3) + Acetic acid (3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (22554-66-1,22554-67-2,25018-27-3,28140-36-5,55676-46-5,58691-31-9,58691-32-0,67772-73-0,74080-42-5,84049-75-2,97058-18-9,103475-61-2)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃;

upstream raw materials:

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

trimethylsilyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

hexanal

acetone