(2R,3R,4S,5R,6R)-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

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-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
• CAS No.: 14257-35-3
• Molecular Formula: C₂₆H₃₅BrO₁₇
• Molecular Weight: 699.458
• Hs Code.: 29400090
• European Community (EC) Number: 634-315-5
• Nikkaji Number: J14.489D
• Mol file: 14257-35-3.mol

Synonyms:14257-35-3;(2R,3R,4S,5R,6R)-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;acetobromomaltose;2,3,6,2',3',6'-Hepta-O-acetyl-a-D-maltosyl bromide;2,3,6,2',3',4',6'-HEPTA-O-ACETYL-A-D-MALTOSYL BROMIDE;SCHEMBL8109512;AKOS015916392;BS-52908;H-1731;J-007667;[(2R,3R,4S,5R,6R)-4,5-bis(acetyloxy)-6-bromo-3-{[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}oxan-2-yl]methyl acetate

Chemical Property of (2R,3R,4S,5R,6R)-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

Chemical Property:

• Appearance/Colour: solid
• Melting Point: 113-114 °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.: −20°C
• 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%,99%, ^*data from raw suppliers

2-3-6-2?-3?-4?-6?-Hepta-O-acetyl-α-D-maltosylbromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 26-36/37/39-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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

Technology Process of (2R,3R,4S,5R,6R)-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

There total 19 articles about (2R,3R,4S,5R,6R)-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 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-nitro-phenyl)-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside]

hexa-O-acetyl-D-maltal

1-azido-1-deoxy-4-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucose

maltose-1-phosphate

Refernces

• 1、 Xu, Lai,Luo, Chin-Hung,Chen, Chien-Sheng. "Halogenation and anomerization of glycopyranoside by TESH/bromine and BHQ/bromine". . p. 315 - 321. Retrieved 2020/07/13.
• 2、 Bachmann, Thomas,Schnurr, Christian,Zainer, Laura,Rychlik, Michael. "Chemical synthesis of 5’-β-glycoconjugates of vitamin B6". supporting information. . Retrieved 2020/02/15.