2-Chloroethyl-2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside

Base Information

• Chemical Name: 2-Chloroethyl-2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside
• CAS No.: 849420-02-6
• Molecular Formula: C₁₆H₂₃ClO₁₀
• Molecular Weight: 410.806
• Mol file: 849420-02-6.mol

Synonyms:2-Chloroethyl-2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside

Chemical Property of 2-Chloroethyl-2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside

Chemical Property:

• PSA: 123.66000
• LogP: 0.32490

Purity/Quality:

98%min ^*data from raw suppliers

2-Chloroethyl-2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Chloroethyl-2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside

There total 9 articles about 2-Chloroethyl-2,3,4,6-tetra-O-acetyl-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: 87.0%

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,121524-01-4,121570-34-1,108032-93-5) + 2-chloro-ethanol (107-07-3) → (2-chloroethyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (849420-02-6)

Guidance literature:

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside; 2-chloro-ethanol; In dichloromethane; at 25 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at 25 ℃; for 1h; Molecular sieve; Inert atmosphere;

With acetic anhydride; In dichloromethane; at 25 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2014.06.021

Reference yield: 80.0%

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,121524-01-4,121570-34-1,108032-93-5) + 2-chloro-ethanol (107-07-3) → (2-chloroethyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (849420-02-6) + 2-chloroethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranoside

Guidance literature:

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside; 2-chloro-ethanol; In dichloromethane; at 25 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at 4 ℃; for 1h; Molecular sieve; Inert atmosphere;

With acetic anhydride; In dichloromethane; at 25 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2014.06.021

Reference yield: 77.0%

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl ortho-allybenzoate + 2-chloro-ethanol (107-07-3) → (2-chloroethyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (849420-02-6) + 3-Iodomethyl-isochroman-1-one (160301-08-6)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 0.5h; Molecular sieve;

DOI:10.1016/j.tetlet.2018.11.061

upstream raw materials:

D-Mannose pentaacetate

2-chloro-ethanol

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

per-O-acetyl-α-D-mannopyranose

Downstream raw materials:

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

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(2-mercaptoethoxy)tetrahydro-2H-pyran-3,4,5-triol

Refernces

• 1、 Schuster, Heiko J.,Vijayakrishnan, Balakumar,Davis, Benjamin G.. "Chain-growth polyglycosylation: Synthesis of linker-equipped mannosyl oligomers". . p. 135 - 141. Retrieved 2015/02/19.
• 2、 Wu, Shanshan,Huang, Xuan,Du, Xuezhong. "Glucose- and pH-responsive controlled release of cargo from protein-gated carbohydrate-functionalized mesoporous silica nanocontainers". supporting information. p. 5580 - 5584. Retrieved 2013/06/27.