2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL BROMIDE

Base Information

• Chemical Name: 2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL BROMIDE
• CAS No.: 114682-36-9
• Molecular Formula: C₃₄H₂₇BrO₉
• Molecular Weight: 659.487
• Mol file: 114682-36-9.mol

Synonyms:b-D-Glucopyranosyl bromide,tetrabenzoate (9CI)

Chemical Property of 2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL BROMIDE

Chemical Property:

• Boiling Point: 729.9±60.0 °C(Predicted)
• PSA: 114.43000
• Density: 1.48±0.1 g/cm3(Predicted)
• LogP: 5.64000

Purity/Quality:

2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL BROMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL BROMIDE

There total 27 articles about 2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL 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%

1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3) → 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide (14218-11-2,14218-30-5,61198-88-7,108438-33-1,108836-02-8,114682-36-9,127305-34-4,151377-77-4)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; at 0 ℃; for 0.75h;

DOI:10.1021/jo051503w

Reference yield: 95.0%

Benzoyl bromide (618-32-6) + (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran (3879-79-6,17791-37-6,19488-61-0,53008-63-2,69237-94-1,69237-95-2,71526-33-5,83462-67-3,84799-77-9,103421-29-0,103421-30-3,139241-42-2,61330-62-9) → 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide (14218-11-2,14218-30-5,61198-88-7,108438-33-1,108836-02-8,114682-36-9,127305-34-4,151377-77-4)

Guidance literature:

With zinc trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/S0008-6215(02)00481-0

Reference yield: 88.0%

1,2,3,4,6-penta-O-benzoyl-α,β-D-mannopyranoside (96996-90-6) → 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide (14218-11-2,14218-30-5,61198-88-7,108438-33-1,108836-02-8,114682-36-9,127305-34-4,151377-77-4)

Guidance literature:

With hydrogen bromide; In dichloromethane; acetic acid; for 12h;

DOI:10.1021/ja00110a010

upstream raw materials:

1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose

1,2,3,4,6-penta-O-benzoyl-α,β-D-mannopyranoside

1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside

Benzoyl bromide

Downstream raw materials:

methyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-benzoyl-α-D-(4-2H)-glucopyranoside

methyl 2,4-di-O-acetyl-3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-6-O-trityl-α-D-mannopyranoside

methyl 2,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3-O-trityl-α-D-mannopyranoside

methyl 2,4-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranoside

Refernces

• 1、 Balzer, Paul G.,Blaszczyk, Stephanie A.,Duan, Xiyan,Ma, Zhi-Xiong,Simmons, Christopher J.,Stevens, Christopher M.,Tang, Weiping,Wang, Hao-Yuan,Wen, Peng,Ye, Wenjing,Yin, Dan. "Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions". supporting information. . Retrieved 2020/02/28.
• 2、 Singh, Yashapal,Demchenko, Alexei V.. "Koenigs–Knorr Glycosylation Reaction Catalyzed by Trimethylsilyl Trifluoromethanesulfonate". supporting information. p. 1461 - 1465. Retrieved 2019/01/04.