2,3,4-TRI-O-ACETYL-ALPHA-L-RHAMNOPYRANOSYL BROMIDE

Base Information

• Chemical Name: 2,3,4-TRI-O-ACETYL-ALPHA-L-RHAMNOPYRANOSYL BROMIDE
• CAS No.: 5158-64-5
• Molecular Formula: C12H17 Br O7
• Molecular Weight: 353.167
• Hs Code.: 2932999099
• Mol file: 5158-64-5.mol

Synonyms:Mannopyranosylbromide, 6-deoxy-, triacetate, a-L- (8CI); Rhamnopyranosyl bromide, triacetate (7CI); a-L-Mannopyranosyl bromide,6-deoxy-, triacetate (9CI); 1-Bromo-2,3,4-tri-O-acetyl-a-L-rhamnose; 2,3,4-Tri-O-acetyl-a-L-rhamnopyranosyl bromide;Acetobromorhamnose; Bromo-L-rhamnose triacetate; a-Acetobromorhamnose

Chemical Property of 2,3,4-TRI-O-ACETYL-ALPHA-L-RHAMNOPYRANOSYL BROMIDE

Chemical Property:

• Melting Point: 71-72 °C
• Boiling Point: 346.1±42.0 °C(Predicted)
• PSA: 88.13000
• Density: 1.46±0.1 g/cm3(Predicted)
• LogP: 0.92120

Purity/Quality:

99% ^*data from raw suppliers

ACETOBROMO-ALPHA-L-RHAMNOSE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-TRI-O-ACETYL-ALPHA-L-RHAMNOPYRANOSYL BROMIDE

There total 27 articles about 2,3,4-TRI-O-ACETYL-ALPHA-L-RHAMNOPYRANOSYL 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%

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose (7404-35-5,17081-04-8,20853-37-6,24332-95-4,27821-10-9,27821-11-0,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,30021-94-4) → 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide (5158-64-5)

Guidance literature:

With hydrogen bromide; acetic anhydride; acetic acid; In dichloromethane; at 20 ℃; diastereoselective reaction;

Reference yield: 99.0%

1,2,3,4-tetra-O-acetyl-6-deoxy-β-D-galactopyranose (34371-41-0) → 2,3,4-tri-O-acetyl-D-fucopyranosyl bromide (5158-64-5,14227-85-1,16741-27-8,24877-07-4,36807-84-8,39524-38-4,41881-45-2,60978-06-5,69483-13-2,69980-52-5,75247-28-8,75247-29-9,80483-13-2,80483-14-3,89301-86-0,96648-29-2,108942-35-4,108942-38-7,138514-69-9,24404-52-2)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1016/S0039-128X(97)00118-9

Reference yield: 96.0%

1,2,3,4-tetra-O-acetyl-D-fucopyranose (51921-33-6) → 2,3,4-tri-O-acetyl-D-fucopyranosyl bromide (5158-64-5,14227-85-1,16741-27-8,24877-07-4,36807-84-8,39524-38-4,41881-45-2,60978-06-5,69483-13-2,69980-52-5,75247-28-8,75247-29-9,80483-13-2,80483-14-3,89301-86-0,96648-29-2,108942-35-4,108942-38-7,138514-69-9,24404-52-2)

Guidance literature:

With hydrogen bromide; In dichloromethane; at 21 ℃; for 0.5h;

DOI:10.1006/bioo.1994.1012

upstream raw materials:

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

1,2,3,4-tetra-O-acetate-β-L-rhamnopyranoside

L-rhamnose

acetic anhydride

Downstream raw materials:

menthyl-rhamnopyranoside

convallatoxin

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-α-D-galactopyranoside

3-hydroxy-2-nitrophenyl 2,3,4-tri-O-acetyl-β-D-fucopyranoside

Refernces

• 1、 Paradas, Miguel,Jurado, Rocio,Haidour, Ali,Robles, Rafael,Justicia, Jose,Cuerva, Juan M.,Rodriguez Granger, Javier,Sampedro Martinez, Antonio,De La Rosa Fraile, Manuel. "Clarifying the structure of granadaene: Total synthesis of related analogue [2]-granadaene and confirmation of its absolute stereochemistry". . p. 6655 - 6661,7. Retrieved 2012.
• 2、 Xu, Kun-Lun,Yu, Lan. "Neuroprotective activity of different monosaccharide-modified gastrodin analogs". . p. 1263 - 1269. Retrieved 2020/01/21.
• 3、 Fang, Jing,Zeng, Jing,Sun, Jiuchang,Zhang, Shuxin,Xiao, Xiong,Lu, Zimin,Meng, Lingkui,Wan, Qian. "Total Syntheses of Resin Glycosides Murucoidins IV and v". supporting information. p. 6213 - 6216. Retrieved 2019/09/04.