Methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-glucopyranoside
• CAS No.: 2641-79-4
• Molecular Formula: C19H46 O6 Si4
• Molecular Weight: 482.913
• DSSTox Substance ID: DTXSID40471250
• Nikkaji Number: J128.056B
• Wikidata: Q82299719
• Mol file: 2641-79-4.mol

Synonyms:2641-79-4;METHYL 2,3,4,6-TETRA-O-(TRIMETHYLSILYL)-ALPHA-D-GLUCOPYRANOSIDE;Methyl 2,3,4,6-tetrakis-O-(trimethylsilyl)hexopyranoside #;SCHEMBL11206262;DTXSID40471250;UIDVFSCIFIMDHO-FQBWVUSXSA-N;.alpha.-D-Glucopyranoside, methyl 2,3,4,6-tetrakis-O-(trimethylsilyl)-;Glucopyranoside, methyl 2,3,4,6-tetrakis-O-(trimethylsilyl)-, .alpha.-D-;J-016417;Methyl galactoside (1S,2R,3S,4R,5R)-, 4TMS derivative;Methyl 2,3,4,6-tetra-O-(trimethylsilyl)- alpha -D-glucopyranoside;Methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-glucopyranoside, 97%;(((2S,3R,4S,5R,6R)-2-Methoxy-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl)tris(oxy))tris(trimethylsilane);[(2S,3R,4S,5R,6R)-2-methoxy-3,5-bis(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-4-yl]oxy-trimethylsilane

Chemical Property of Methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-glucopyranoside

Chemical Property:

• Boiling Point: 109-110 °C(Press: 0.1 Torr)
• PSA: 55.38000
• Density: 0.95±0.1 g/cm3(Predicted)
• LogP: 4.86950
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 482.23714532
• Heavy Atom Count: 29
• Complexity: 507

Purity/Quality:

97% ^*data from raw suppliers

METHYL-2,3,4,6-TETRA-O-(TRIMETHYLSILYL)-ALPHA-D-GLUCOPYRANOSIDE 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C

Technology Process of Methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-glucopyranoside

There total 14 articles about Methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-glucopyranoside 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%

chloro-trimethyl-silane (75-77-4) + methyl-alpha-D-glucopyranoside (97-30-3) → methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside (2641-79-4)

Guidance literature:

With pyridine; at 50 - 60 ℃; for 1h;

DOI:10.1016/0008-6215(92)80082-C

Reference yield: 100.0%

1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) + methyl-alpha-D-glucopyranoside (97-30-3) → methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside (2641-79-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1002/ejoc.201101267

Reference yield: 95.0%

N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + methyl-alpha-D-glucopyranoside (97-30-3) → methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside (2641-79-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0008-6215(92)84254-P

upstream raw materials:

chloro-trimethyl-silane

methyl-alpha-D-glucopyranoside

N,O-bis-(trimethylsilyl)-acetamide

trimethylsilyl cyanide

Downstream raw materials:

phenyl-1-thio-α-D-glucopyranoside

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

1,4-anhydro-D-glucitol

1,5-anhydro-D-glucitol

Refernces

• 1、 Holmstr?m, Thomas,Galsgaard Malle, Mette,Wu, Shunliang,Jensen, Knud J?rgen,Hatzakis, Nikos S.,Pedersen, Christian Marcus. "Carbohydrate-Derived Metal-Chelator-Triggered Lipids for Liposomal Drug Delivery". . p. 6917 - 6922. Retrieved 2021.
• 2、 Shipton, Megan L.,Riley, Andrew M.,Rossi, Ana M.,Brearley, Charles A.,Taylor, Colin W.,Potter, Barry V. L.. "Both d - And l -Glucose Polyphosphates Mimic d - myo-Inositol 1,4,5-Trisphosphate: New Synthetic Agonists and Partial Agonists at the Ins(1,4,5)P3Receptor". . p. 5442 - 5457. Retrieved 2020/07/21.