2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate
• CAS No.: 93221-21-7
• Molecular Formula: C15H19 N O9 S
• Molecular Weight: 389.383
• Mol file: 93221-21-7.mol

Synonyms:2,3,4,6-Tetra-O-acetyl-伪-D-mannopyranosyl isothiocyanate

Chemical Property of 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate

Chemical Property:

• Melting Point: 81-82 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 469.7±45.0 °C(Predicted)
• PSA: 158.88000
• Density: 1.40±0.1 g/cm3(Predicted)
• LogP: 0.17230

Purity/Quality:

99% ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyl isothiocyanate ^*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-acetyl-α-D-mannopyranosyl isothiocyanate

There total 21 articles about 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate 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: 83.0%

2-methyl-4,5-dihydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-galactopyrano)[2,1-d]-2-oxazoline (943860-86-4) + thiophosgene (463-71-8) → 2,3,4,6-tetra-O-Acetyl-β-D-galactopyranosyl isothiocyanate (14152-97-7,18866-59-6,93221-21-7,121959-10-2,121959-11-3,122564-52-7,41135-18-6)

Guidance literature:

With calcium carbonate; In dichloromethane; water; at 25 ℃; for 1h;

DOI:10.1021/jo062419z

Reference yield: 82.0%

potassium thioacyanate (333-20-0) + acetobromomannose (13242-53-0) → 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate (93221-21-7)

Guidance literature:

With 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; In acetonitrile; for 3h; Heating;

DOI:10.1055/s-2004-829074

Reference yield: 81.0%

trimethylsilyl isothiocyanate (2290-65-5) + penta-O-acetyl-α-D-galactopyranose (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-β-D-galactopyranosyl isothiocyanate (14152-97-7,18866-59-6,93221-21-7,121959-10-2,121959-11-3,122564-52-7,41135-18-6)

Guidance literature:

With tin(IV) chloride; In dichloromethane; for 24h; Heating;

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide

potassium thioacyanate

2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl chloride

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide

Downstream raw materials:

2,3,4,6-tetra-O-acetyl-1-N--β-D-galactopyranosylamine

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylamine

N-(ε-aminocaproyl)-β-D-galactopyranosylamine

Refernces

• 1、 Mangte, Anvita D.,Nayak, Riddhi A.. "Synthesis and Antimicrobial Activities of 1,2,4-Thiadiazolidin-3-thione Hydrochlorides". . p. 77 - 83. Retrieved 2022/03/27.
• 2、 Avvakumova, Svetlana,Fezzardi, Paola,Pandolfi, Laura,Colombo, Miriam,Sansone, Francesco,Casnati, Alessandro,Prosperi, Davide. "Gold nanoparticles decorated by clustered multivalent cone-glycocalixarenes actively improve the targeting efficiency toward cancer cells". supporting information. p. 11029 - 11032. Retrieved 2014/11/07.