BETA,BETATREHALOSE OCTAACETATE

Base Information

• Chemical Name: BETA,BETATREHALOSE OCTAACETATE
• CAS No.: 55676-46-5
• Molecular Formula: C28H38O19
• Molecular Weight: 678.59
• Mol file: 55676-46-5.mol

Synonyms:BETA,BETATREHALOSE OCTAACETATE;SS,SSTREHALOSE OCTAACETATE

Chemical Property of BETA,BETATREHALOSE OCTAACETATE

Chemical Property:

• PSA: 238.09000
• LogP: -0.83080

Purity/Quality:

95% ^*data from raw suppliers

BETA-BETATREHALOSE OCTAACETATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BETA,BETATREHALOSE OCTAACETATE

There total 26 articles about BETA,BETATREHALOSE OCTAACETATE 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: 81.0%

Acetic acid (2S,3aR,5R,6R,7S,7aR)-6-acetoxy-5-acetoxymethyl-2-methyl-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester → 2,3,4,6-tetra-O-acetyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-β-D-glucopyranoside (55676-46-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 1h;

DOI:10.1016/S0040-4039(98)02626-4

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

upstream raw materials:

2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

β,β-trehalose

acetic anhydride

Downstream raw materials:

β,β-trehalose

neotrehalose

Refernces

• 1、 Wang,Kong. "A highly stereocontrolled synthesis of 1β,1β-linked acetylated oligosaccharides via orthoester formation-rearrangement". . p. 1361 - 1364. Retrieved 1999.
• 2、 Repetto, Evangelina,Manzano, Veronica E.,Uhrig, Maria Laura,Varela, Oscar. "Synthesis of branched dithiotrisaccharides via ring-opening reaction of sugar thiiranes". . p. 253 - 265. Retrieved 2012/02/14.