methyl (3S,5R,6R)-3,4,5-triacetyloxy-6-bromanyl-oxane-2-carboxylate

Base Information

• Chemical Name: methyl (3S,5R,6R)-3,4,5-triacetyloxy-6-bromanyl-oxane-2-carboxylate
• CAS No.: 21085-72-3
• Molecular Formula: C13H17BrO9
• Molecular Weight: 397.177
• Hs Code.: 29189900
• European Community (EC) Number: 244-203-4
• Mol file: 21085-72-3.mol

Synonyms:21085-72-3;SCHEMBL13830203;A815129;(3S,5R,6R)-3,4,5-triacetyloxy-6-bromo-2-oxanecarboxylic acid methyl ester;methyl (3S,5R,6R)-3,4,5-triacetyloxy-6-bromanyl-oxane-2-carboxylate

Chemical Property of methyl (3S,5R,6R)-3,4,5-triacetyloxy-6-bromanyl-oxane-2-carboxylate

Chemical Property:

• Appearance/Colour: White Crystalline Solid
• Vapor Pressure: 3.02E-06mmHg at 25°C
• Melting Point: 80-110°C(lit.)
• Refractive Index: 1.504
• Boiling Point: 388.6 °C at 760 mmHg
• Flash Point: 188.8 °C
• PSA: 114.43000
• Density: 1.52g/cm³
• LogP: 0.07430
• Storage Temp.: −20°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly, Heated, Sonicated), Dichlorometha
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 396.00559
• Heavy Atom Count: 23
• Complexity: 492

Purity/Quality:

98% ^*data from raw suppliers

Acetobromo-a-D-glucuronic Acid, Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC(C1OC(=O)C)Br)C(=O)OC)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@H]1[C@H](OC([C@H](C1OC(=O)C)OC(=O)C)C(=O)OC)Br
• Uses: Acetobromo-α-D-glucuronic acid methyl ester is used for the synthesis of HMR1098-S-glucuronide methyl ester, a new K-ATP-blocking agent being developed as a drug for prevention of sudden cardiac death. Acetobromo-α-D-glucuronic acid methyl ester is used for the synthesis of water-soluble glucuronide derivatives of Camptothecin, which is used for cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy (ADEPT). Acetobromo-α-D-glucuronic acid methyl ester is used for the synthesis of glucuronide prodrug compounds of Janus kinase (JAK) inhibitor tofacitinib, which could be cleaved by β-glucuronidase enzymes such as those produced by the microbiome in the gastrointestinal tract, thereby increasing levels of tofacitinib at the site of gastrointestinal inflammation and limiting the systemic exposure of tofacitinib when treating localized inflammatory diseases.

Technology Process of methyl (3S,5R,6R)-3,4,5-triacetyloxy-6-bromanyl-oxane-2-carboxylate

There total 29 articles about methyl (3S,5R,6R)-3,4,5-triacetyloxy-6-bromanyl-oxane-2-carboxylate 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%

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3) → 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3)

Guidance literature:

With hydrogen bromide; acetic anhydride; at 0 - 20 ℃; for 2h; Inert atmosphere;

Reference yield: 96.98%

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2) → 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3)

Guidance literature:

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

DOI:10.1016/j.bmcl.2015.12.072

Reference yield: 88.0%

methyl (3,4-di-O-tert-butyldimethylsilyl-D-glucuronate)glycal (252000-90-1) → 3,4-di-O-(tert-butyldimethylsilyl)-D-glucuronal (161851-34-9) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3)

Guidance literature:

With potassium hydroxide; In methanol; at 0 - 20 ℃;

DOI:10.1016/j.carres.2013.01.007

upstream raw materials:

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl 1,2,3,4-tetraacetyl-α-D-glucopyranuronate

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate

Downstream raw materials:

4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate

p-nitrobenzyl-2,3,4-tri-O-acetyl-beta-D-glucuronic acid methyl ester

2,3,4-Tri-O-acetyl-1-mercaptomethyl-β-D-glucopyranuronsaeure-methylester

methyl {(17-oxo-1,3,5[10]-estratrien-3-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate