2,3,5,6-Tetrakis-O-(trimethylsilyl)-L-ascorbic acid

Base Information

• Chemical Name: 2,3,5,6-Tetrakis-O-(trimethylsilyl)-L-ascorbic acid
• CAS No.: 55517-56-1
• Molecular Formula: C18H40O6Si4
• Molecular Weight: 464.85
• DSSTox Substance ID: DTXSID101345363
• Nikkaji Number: J146.371C
• Mol file: 55517-56-1.mol

Synonyms:SCHEMBL3837179;DTXSID101345363;55517-56-1;2,3,5,6-Tetrakis-O-(trimethylsilyl)-L-ascorbic acid

Chemical Property of 2,3,5,6-Tetrakis-O-(trimethylsilyl)-L-ascorbic acid

Chemical Property:

• PSA: 63.22000
• LogP: 4.89800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 464.19019513
• Heavy Atom Count: 28
• Complexity: 593

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C[Si](C)(C)OCC(C1C(=C(C(=O)O1)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C
• Isomeric SMILES: C[Si](C)(C)OC[C@@H]([C@@H]1C(=C(C(=O)O1)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C

Technology Process of 2,3,5,6-Tetrakis-O-(trimethylsilyl)-L-ascorbic acid

There total 1 articles about 2,3,5,6-Tetrakis-O-(trimethylsilyl)-L-ascorbic acid 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: 99.0%

1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) + ascorbic acid (50-81-7,98966-42-8) → 2,3,5,6-tetrakis-O-(trimethylsilyl) ascorbate (55517-56-1)

Guidance literature:

1,1,1,3,3,3-hexamethyl-disilazane; ascorbic acid; trifluorormethanesulfonic acid; In tetrahydrofuran; at 66 - 70 ℃; for 6h;

With calcium carbonate; In tetrahydrofuran; for 2h;

With 1,1,1,3,3,3-hexamethyl-disilazane; at 70 ℃; Product distribution / selectivity;

Reference yield:

2,3,5,6-tetrakis-O-(trimethylsilyl) ascorbate (55517-56-1) → tricyclohexylammonium salt of L-ascorbic acid 2-O-phosphate (82134-96-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Br₂, 2.) dimethyl phosphonate / 1.) CH₂Cl₂, room temperature, 1 h, 2.) room temperature, overnight

2: 1.) TMSP / 1.) 105 deg C, 5 h, 2.) ether, CH₃OH, room temperature to 0 deg C

With Tris(trimethylsilyl) phosphate; bromine; Dimethyl phosphite;

DOI:10.1021/jo00139a014

upstream raw materials:

1,1,1,3,3,3-hexamethyl-disilazane

ascorbic acid

Downstream raw materials:

tricyclohexylammonium salt of L-ascorbic acid 2-O-phosphate

Refernces

• 1、 -. "Ester Derivatives of Ascorbic and 2-Keto Acid Saccharides". Page/Page column 8. . Retrieved 2008/12/05.
• 2、 Sekine, Mitsuo,Futatsugi, Tetsuaki,Hata, Tsujiaki,Cramer, Friedrich. "Silyl Phosphites. 21. A New Method for the Synthesis of L-Ascorbic Acid 2-O-Phosphate by Utilizing Phosphoryl Rearrangement". . p. 3453 - 3456. Retrieved 2007/10/02.