Propargyl a-D-mannopyranoside

Base Information

• Chemical Name: Propargyl a-D-mannopyranoside
• CAS No.: 854262-01-4
• Molecular Formula: C9H14O6
• Molecular Weight: 218.207
• Hs Code.: 2938909090
• Mol file: 854262-01-4.mol

Synonyms:Propargyl a-D-mannopyranoside;1-(2'-Propargyl)-alpha-D-mannose;2-Propyn-1-yl alpha-D-mannopyranoside;2-Propynyl alpha-D-mannopyranoside;Propargyl alpha-D-mannopyranoside

Chemical Property of Propargyl a-D-mannopyranoside

Chemical Property:

• Melting Point: 117-118 °C
• Boiling Point: 452.5±45.0 °C(Predicted)
• PKA: 12.79±0.70(Predicted)
• PSA: 99.38000
• Density: 1.45±0.1 g/cm3(Predicted)
• LogP: -2.56390
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Propargyl a-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Propargyl a-D-mannopyranoside

There total 15 articles about Propargyl a-D-mannopyranoside 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%

propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (83476-52-2) → propargyl α-D-mannopyranoside (854262-01-4)

Guidance literature:

With sodium methoxide; In methanol; at 25 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ja403323y

Reference yield: 76.0%

D-Mannose (530-26-7) + propargyl alcohol (107-19-7) → propargyl α-D-mannopyranoside (854262-01-4)

Guidance literature:

With aminosulfonic acid; at 80 ℃; for 3h; Neat (no solvent);

DOI:10.1016/j.catcom.2011.07.016

Reference yield:

per-O-acetyl-α-D-mannopyranose (4163-65-9) → propargyl α-D-mannopyranoside (854262-01-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / BF₃*OEt₂ / CH₂Cl₂ / 16 h / Heating

2: MeONa / methanol / 1 h / 20 °C / pH 7

With boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane; 2: Zemplen de-O-acetylation;

DOI:10.1021/ol016975l

upstream raw materials:

propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

D-Mannose

propargyl alcohol

per-O-acetyl-α-D-mannopyranose

Downstream raw materials:

4-phenyl-1,7-bis-O-[2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl]hep-2,5-diyn-1,4,7-triol

1,7-bis-O-[2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl]-4-(p-4-tert-butylphenyloxymethyl)-hep-2,5-diyn-1,4,7-triol

2-oxopropyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

allyl α-D-mannopyranoside

Refernces

• 1、 Reintjens, Niels R. M.,Tondini, Elena,Vis, Christopher,McGlinn, Toroa,Meeuwenoord, Nico J.,Hogervorst, Tim P.,Overkleeft, Herman S.,Filippov, Dmitri V.,van der Marel, Gijsbert A.,Ossendorp, Ferry,Codée, Jeroen D. C.. "Multivalent, Stabilized Mannose-6-Phosphates for the Targeted Delivery of Toll-Like Receptor Ligands and Peptide Antigens". . p. 434 - 440. Retrieved 2021.
• 2、 ?ezanka, Michal,Dolensky, Bohumil,Krabicová, Ilona. "Selectivity of 1-O-Propargyl-D-Mannose Preparations". . . Retrieved 2022/03/01.
• 3、 Spitzer, Lea,Lecommandoux, Sébastien,Cramail, Henri,Jér?me, Fran?ois. "Sequential acid-catalyzed alkyl glycosylation and oligomerization of unprotected carbohydrates". . p. 1361 - 1369. Retrieved 2021/02/26.