2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl N,N,N',N'-Tetramethylphosphorodiamidate

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl N,N,N',N'-Tetramethylphosphorodiamidate
• CAS No.: 143520-19-8
• Molecular Formula: C38H47 N2 O7 P
• Molecular Weight: 674.76
• DSSTox Substance ID: DTXSID20455634
• Nikkaji Number: J863.505F
• Wikidata: Q82277725
• Mol file: 143520-19-8.mol

Synonyms:143520-19-8;2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl N,N,N',N'-Tetramethylphosphorodiamidate;2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYL N,N,N',N'-TETRAMETHYLPHOSPHORODIAMIDATE (CA. 20% IN BENZENE);N-[dimethylamino-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyphosphoryl]-N-methylmethanamine;DTXSID20455634;RTYAYXUZHPWJOK-JTDOPDNRSA-N;MFCD06797176;T2197;T71771;J-007826;1-O-[Bis(dimethylamino)phosphinyl]-2-O,3-O,4-O,6-O-tetrabenzyl-alpha-D-glucopyranose;2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYLN,N,N',N'-TETRAMETHYLPHOSPHORODIAMIDATE(CA.20%INBENZENE)

Chemical Property of 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl N,N,N',N'-Tetramethylphosphorodiamidate

Chemical Property:

• Boiling Point: 729.844oC at 760 mmHg
• Flash Point: 395.196oC
• PSA: 88.74000
• Density: 1.22g/cm3
• LogP: 6.93220
• Storage Temp.: Refrigerator
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 17
• Exact Mass: 674.31208884
• Heavy Atom Count: 48
• Complexity: 920

Purity/Quality:

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

2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosylN,N,N’,N’-tetramethylphosphorodiamidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)P(=O)(N(C)C)OC1C(C(C(C(O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Isomeric SMILES: CN(C)P(=O)(N(C)C)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Uses: 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl N,N,N’,N’-tetramethylphosphorodiamidate (CAS# 143520-19-8) is a carbohydrate used in the synthesis of oligosaccharides acting as a glycosyl acceptor with its phosphorous moiety acting as a leaving group.

Technology Process of 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl N,N,N',N'-Tetramethylphosphorodiamidate

There total 2 articles about 2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl N,N,N',N'-Tetramethylphosphorodiamidate 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:

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) + N,N,N',N'-Tetramethylphosphorodiamidic chloride (1605-65-8) → C38H47N2O7P (143520-19-8)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; at -10 ℃; for 2h;

DOI:10.1016/S0040-4039(97)01122-2

Reference yield:

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) + N,N,N',N'-Tetramethylphosphorodiamidic chloride (1605-65-8) → C38H47N2O7P (143520-27-8) + C38H47N2O7P (143520-19-8)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, hexane, -78 deg C, 15 min, 2) HMPA, a) to -30 deg C, 0.5 h, b) -30 deg C, 2 h;

DOI:10.1016/S0040-4039(00)92679-0

Reference yield: 89.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + C38H47N2O7P (143520-19-8) → methyl O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (84799-76-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In various solvent(s); at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)92679-0

upstream raw materials:

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

N,N,N',N'-Tetramethylphosphorodiamidic chloride

Downstream raw materials:

methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside

methyl O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

cholesteryl α- and β-2,3,4,6-tetra-O-benzyl-D-glucosides