2,3,4,6-Tetra-o-acetyl-alpha-d-mannopyranosyl bromide

Base Information

• Chemical Name: 2,3,4,6-Tetra-o-acetyl-alpha-d-mannopyranosyl bromide
• CAS No.: 13242-53-0
• Molecular Formula: C14H19BrO9
• Molecular Weight: 411.203
• Hs Code.: 2938909090
• DSSTox Substance ID: DTXSID40454088
• Nikkaji Number: J81.578K
• Wikidata: Q82275422
• Mol file: 13242-53-0.mol

Synonyms:13242-53-0;Acetobromomannose;2,3,4,6-tetra-o-acetyl-alpha-d-mannopyranosyl bromide;Bromo 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranoside;(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate;[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate;Bromo 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranoside(Stabilized with 4per cent CaCO3);Tetra-O-acetyl-alpha-D-mannosyl bromide;SCHEMBL143602;(Stabilized with 4% CaCO3);DTXSID40454088;CYAYKKUWALRRPA-DGTMBMJNSA-N;MFCD00190698;AKOS027326677;GS-5958;.alpha.-D-Mannopyranosyl bromide, tetraacetate;H10049;T-2352;A888296;2,3,4,6-tetra-O-acetyl-1-Bromo-alpha-D- mannose;Bromo 2,3,4,6-Tetra-O-acetyl-?-D-mannopyranoside;J-006176;2,3,4,6-Tetra-o-acetyl-alpha-d-mannopyranosylbromide;alpha-D-Mannopyranosyl bromide, 2,3,4,6-tetraacetate;Bromo 2,3,4,6-Tetra-O-acetyl- alpha -D-mannopyranoside;(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyltriacetate;[(2R,3R,4S,5S,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate

Chemical Property of 2,3,4,6-Tetra-o-acetyl-alpha-d-mannopyranosyl bromide

Chemical Property:

• Melting Point: 60-61°C
• Boiling Point: 412.007 °C at 760 mmHg
• Flash Point: 202.975 °C
• PSA: 114.43000
• Density: 1.49 g/cm³
• LogP: 0.46440
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 410.02124
• Heavy Atom Count: 24
• Complexity: 507

Purity/Quality:

98%, ^*data from raw suppliers

Bromo2,3,4,6-Tetra-O-acetyl-α-D-mannopyranoside(Stabilizedwith4%CaCO3) ^*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)Br)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)Br)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 2,3,4,6-Tetra-o-acetyl-alpha-d-mannopyranosyl bromide

There total 46 articles about 2,3,4,6-Tetra-o-acetyl-alpha-d-mannopyranosyl bromide 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%

β-D-glucose pentaacetate (604-69-3) → 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.bioorg.2021.105479

Reference yield: 100.0%

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3)

Guidance literature:

With hydrogen bromide; In acetic acid; at 20 ℃; Sealed tube;

Reference yield: 83.0%

D-Glucose (2280-44-6) + acetic anhydride (108-24-7) → 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3)

Guidance literature:

D-Glucose; acetic anhydride; With perchloric acid; at 20 ℃; for 4h;

With phosphorus; bromine; In water; at 20 ℃; for 3h;

DOI:10.1007/s10600-016-1721-5

upstream raw materials:

β-D-mannopyranose pentaacetate

D-Mannose pentaacetate

2,3,4,6-tetra-O-acetyl-D-mannopyranose

per-O-acetyl-α-D-mannopyranose

Downstream raw materials:

(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triyl triacetate

(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)benzene

tetra-O-acetyl-N-p-tolyl-α-D-mannopyranosylamine

tetra-O-acetyl-N-p-tolyl-β-D-mannopyranosylamine

Refernces

• 1、 Han, Liwen,Sheng, Wenlong,Li, Xiaobin,Sik, Attila,Lin, Houwen,Liu, Kechun,Wang, Lizhen. "Novel carbohydrate modified berberine derivatives: Synthesis and: In vitro anti-diabetic investigation". . p. 598 - 605. Retrieved 2019.
• 2、 Bari, Ahmed,Alanazi, Amer M.,Syed, Saeed Ali,Al-Obaid, Abdulrahman M.,Al-Jabal, Maher M.,Fun, Hoong-Kun. "A short route for large-scale synthesis of per-O-acetylated C-1 hydroxyglycopyranose". . p. 3786 - 3788. Retrieved 2015.
• 3、 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.
• 4、 Nerella, Srinivas,Kankala, Shravankumar,Gavaji, Brahmeshwari. "Synthesis of podophyllotoxin-glycosyl triazoles via click protocol mediated by silver (I)-N-heterocyclic carbenes and their anticancer evaluation as topoisomerase-II inhibitors". supporting information. p. 9 - 16. Retrieved 2019/06/27.