[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-bromooxan-3-yl]oxyoxan-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-bromooxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS No.: 4753-07-5
• Molecular Formula: C26H35 Br O17
• Molecular Weight: 699.458
• Hs Code.: 2938909090
• DSSTox Substance ID: DTXSID50456432
• Nikkaji Number: J502.388B
• Wikidata: Q82278905
• Mol file: 4753-07-5.mol

Synonyms:4753-07-5;[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-bromooxan-3-yl]oxyoxan-2-yl]methyl acetate;Bromo Heptaacetyl-D-lactoside, Stabilized with 4% Calcium Carbonate;2,2',3,3',4',6,6'-HEPTA-O-ACETYL-alpha-D-LACTOSYL BROMIDE;FT-0663746;SCHEMBL17589151;ACETOBROMO-ALPHA-D-LACTOSE;DTXSID50456432;NLFHLQWXGDPOME-NDMRNNIMSA-N;CS-0452826;H-1730;2,3,6,2 ,3 ,4 ,6 -Hepta-O-acetyl-a-D-cellobiosyl bromide;2,2,3,3,4,6,6-HEPTA-O-ACETYL-ALPHA-D-LACTOSYLBROMIDE;(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate;(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate;2-O,3-O,6-O-Triacetyl-4-O-(2-O,3-O,4-O,6-O-tetraacetyl-beta-D-galactopyranosyl)-alpha-D-glucopyranosyl bromide

Chemical Property of [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-bromooxan-3-yl]oxyoxan-2-yl]methyl acetate

Chemical Property:

• Melting Point: 140-141°C
• Boiling Point: 659.5±55.0 °C(Predicted)
• PSA: 211.79000
• Density: 1.47±0.1 g/cm3(Predicted)
• LogP: 0.00100
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Sensitive.: Hygroscopic
• Solubility.: Soluble in chloroform
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 18
• Exact Mass: 698.10576
• Heavy Atom Count: 44
• Complexity: 1090

Purity/Quality:

98% ^*data from raw suppliers

BromoHeptaacetyl-D-lactoside,Stabilizedwith4%CalciumCarbonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC2C(OC(C(C2OC(=O)C)OC(=O)C)Br)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2OC(=O)C)OC(=O)C)Br)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: Bromo Heptaacetyl-D-lactoside, Stabilized with 4% Calcium Carbonate (cas# 4753-07-5) is a compound useful in organic synthesis.

Technology Process of [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-bromooxan-3-yl]oxyoxan-2-yl]methyl acetate

There total 34 articles about [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-bromooxan-3-yl]oxyoxan-2-yl]methyl acetate 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%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate (22352-19-8) → 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide (4753-07-5,5160-10-1,14206-57-6,14227-66-8,14257-35-3,42385-75-1,67650-37-7,68682-05-3,69308-57-2,69349-74-2,70223-96-0,70223-97-1,71276-38-5,85248-99-3,118493-15-5,120575-76-0)

Guidance literature:

With hydrogen bromide; acetic acid; for 3h; Ambient temperature;

DOI:10.1021/jo00062a020

Reference yield: 95.1%

2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranose (18464-08-9,66073-13-0,71623-44-4,101981-29-7,109922-72-7,109922-73-8,132287-75-3,132287-76-4,132287-78-6,132303-63-0,134311-82-3,134333-39-4) → 2,2',3,3',4',6,6'-hepta-O-acetyl-β-D-cellobiosyl bromide (70223-96-0,4753-07-5,5160-10-1,14206-57-6,14227-66-8,14257-35-3,42385-75-1,67650-37-7,68682-05-3,69308-57-2,69349-74-2,70223-97-1,71276-38-5,85248-99-3,118493-15-5,120575-76-0)

Guidance literature:

With hydrogen bromide; In chloroform; acetic acid; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2013.12.062

Reference yield: 92.0%

2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-D-glucopyranose (18464-08-9,66073-13-0,71623-44-4,101981-29-7,109922-72-7,109922-73-8,132287-75-3,132287-76-4,132287-78-6,132303-63-0,134311-82-3,134333-39-4) → 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide (4753-07-5,5160-10-1,14206-57-6,14227-66-8,14257-35-3,42385-75-1,67650-37-7,68682-05-3,69308-57-2,69349-74-2,70223-96-0,70223-97-1,71276-38-5,85248-99-3,118493-15-5,120575-76-0)

Guidance literature:

With tris(2,2'-bipyridyl)ruthenium dichloride; carbon tetrabromide; tetrabutylammomium bromide; In N,N-dimethyl-formamide; Schlenk technique; Sealed tube; Inert atmosphere; Irradiation;

DOI:10.1055/s-0033-1340493

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate

2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-D-glucopyranose

1,2,3,6,2',3',4',6'-octa-O-acetylmaltose

D-maltose octaacetate

Downstream raw materials:

4-nitrophenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tetra-O-acetyl-β-D-glucopyranoside

2,3,6,2',3',4'6'-hepta-O-acetyl-β-D-lactopyranosyl isothiocianate

4-formyl-2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-(benzyloxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Refernces

• 1、 Krol, Ewelina,Pastuch-Gawolek, Gabriela,Nidzworski, Dawid,Rychlowski, Michal,Szeja, Wieslaw,Grynkiewicz, Grzegorz,Szewczyk, Boguslaw. "Synthesis and antiviral activity of a novel glycosyl sulfoxide against classical swine fever virus". . p. 2662 - 2670. Retrieved 2014.
• 2、 Li, Xiao-San,Chen, Tang-Ji,Xu, Zhi-Peng,Long, Juan,He, Miao-Ying,Zhan, He-Hui,Zhuang, Hai-Cai,Wang, Qi-Lin,Liu, Li,Yang, Xue-Mei,Tang, Jin-Shan. "Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents". . . Retrieved 2021/12/30.
• 3、 Nayak, Riddhi A.,Mangte, Anvita D.. "Synthesis and antimicrobial studies of novel n-glycosyl hydrazino carbothioamide". . p. 127 - 131. Retrieved 2021/01/06.