2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate
• CAS No.: 74808-09-6
• Molecular Formula: C36H36 Cl3 N O6
• Molecular Weight: 685.044
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID10453689
• Nikkaji Number: J639.605D
• Wikidata: Q82274890
• Mol file: 74808-09-6.mol

Synonyms:74808-09-6;2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate;(2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate;2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl trichloroacetimidate;[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 2,2,2-trichloroethanimidate;C36H36Cl3NO6;SCHEMBL3386829;DTXSID10453689;2,3,4,6-Tetra-O-benzyl-D-glucopyranosyl trichloroacetimidate;MFCD03427010;AKOS015889374;AS-71301;2 3 4 6-TETRA-O-BENZYL-alpha-D-GLUCOPYR&;A934059;2,3,4,6-Tetra-O-benzyl- alpha -D-glucopyranosyl trichloroacetimidate;2-O,3-O,4-O,6-O-Tetrabenzyl-alpha-D-glucopyranose trichloroacetimidate;(2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl2,2,2-trichloroacetimidate;(2R,3R,4S,5R,6R)-3,4,5-TRIS(BENZYLOXY)-6-[(BENZYLOXY)METHYL]OXAN-2-YL 2,2,2-TRICHLOROETHANIMIDATE

Chemical Property of 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate

Chemical Property:

• Melting Point: 69-74 °C(lit.)
• Boiling Point: 696.0±65.0 °C(Predicted)
• PKA: 1.39±0.70(Predicted)
• PSA: 79.23000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 8.14810
• Storage Temp.: −20°C
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 15
• Exact Mass: 683.160821
• Heavy Atom Count: 46
• Complexity: 868

Purity/Quality:

98% ^*data from raw suppliers

2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl trichloroacetimidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C(C(O2)OC(=N)C(Cl)(Cl)Cl)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)OC(=N)C(Cl)(Cl)Cl)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5

Technology Process of 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate

There total 49 articles about 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate 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%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + trichloroacetonitrile (545-06-2) → 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6)

Guidance literature:

In dichloromethane; at 0 ℃; for 1h; Molecular sieve;

DOI:10.1021/acs.jmedchem.0c00841

Reference yield: 100.0%

2,3,4,6-tetra-O-benzyl-D-mannopyranose (4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5) + trichloroacetonitrile (545-06-2) → 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate (74808-09-6,90357-89-4,90358-01-3,103368-01-0,103368-04-3,103368-06-5,104048-30-8,104048-33-1,114743-70-3,132201-75-3,132748-02-8,83441-60-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1055/s-0029-1218772

Reference yield: 98.0%

2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,78609-16-2) + trichloroacetonitrile (545-06-2) → 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate (74808-09-6,90357-89-4,90358-01-3,103368-01-0,103368-04-3,103368-06-5,104048-30-8,104048-33-1,114743-70-3,132201-75-3,132748-02-8,83441-60-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1039/b414119a

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

trichloroacetonitrile

2,3,4,6-tetra-O-benzyl-D-glucopyranoside

2,3,4,6-tetra-O-benzyl-D-glucopyranose

Downstream raw materials:

1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose

2-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)thiophen

(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran

methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside

Refernces

• 1、 Schmidt, Richard R.,Michel, Josef. "DIRECT O-GLYCOSYL TRICHLOROACETIMIDATE FORMATION. NUCLEOPHILICITY OF THE ANOMERIC OXYGEN ATOM". . p. 821 - 824. Retrieved 1984.
• 2、 Holmstr?m, Thomas,Nielsen, Michael Martin,Pedersen, Christian Marcus. "Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**". supporting information. . Retrieved 2021/12/30.
• 3、 Song, Wei,Sun, Yong,Xu, Lintao,Sun, Yajing,Li, Tianlu,Peng, Peng,Lou, Hongxiang. "Synthesis of nature product kinsenoside analogues with anti-inflammatory activity". supporting information. . Retrieved 2020/12/02.