6-O-(tert-Butyldimethylsilyl)-D-glucal

Base Information

• Chemical Name: 6-O-(tert-Butyldimethylsilyl)-D-glucal
• CAS No.: 58871-09-3
• Molecular Formula: C12H24O4Si
• Molecular Weight: 260.406
• DSSTox Substance ID: DTXSID50452257
• Nikkaji Number: J1.409.402D,J1.466.428I
• Wikidata: Q82272763
• Mol file: 58871-09-3.mol

Synonyms:58871-09-3;6-O-(tert-Butyldimethylsilyl)-D-glucal;6-O-tert-butyldimethylsilyl-D-glucal;(2R,3S,4R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-3,4-diol;(2R,3S,4R)-2-(((tert-Butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol;SCHEMBL1578986;DTXSID50452257;HYSBQWOHQIVUQQ-MXWKQRLJSA-N;6-O-tert-Butyldimethylsilyl glucal;MFCD09756139;6-O-(tert-Butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-glucopyranose;6-O-(tert-Butyldimethylsilyl)-1,2-dideoxy-1,2-didehydro-D-arabino-hexopyranose

Chemical Property of 6-O-(tert-Butyldimethylsilyl)-D-glucal

Chemical Property:

• Refractive Index: n20/D 1.485(lit.)
• Flash Point: >230 °F
• PSA: 58.92000
• Density: 1.06 g/mL at 25 °C(lit.)
• LogP: 1.64250
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 260.14438578
• Heavy Atom Count: 17
• Complexity: 283

Purity/Quality:

98%Min ^*data from raw suppliers

(2R,3S,4R)-2-(((tert-Butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC1C(C(C=CO1)O)O
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OC[C@@H]1[C@H]([C@@H](C=CO1)O)O

Technology Process of 6-O-(tert-Butyldimethylsilyl)-D-glucal

There total 8 articles about 6-O-(tert-Butyldimethylsilyl)-D-glucal 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: 94.0%

tert-butyldimethylsilyl chloride (18162-48-6) + D-glucal (13265-84-4) → 6-O-tert-butyldimethylsilyl-D-glucal (58871-09-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 12h;

DOI:10.1021/jo00248a010

Reference yield: 89.0%

N,O-bis(tertbutyldimethylsilyl)acetamide (82112-21-8) + D-glucal (13265-84-4) → 6-O-tert-butyldimethylsilyl-D-glucal (58871-09-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1016/0040-4039(95)02232-5

Reference yield: 70.0%

t-butyldimethylsiyl triflate (69739-34-0) + D-glucal (13265-84-4) → 6-O-tert-butyldimethylsilyl-D-glucal (58871-09-3)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1021/ol991176c

upstream raw materials:

tert-butyldimethylsilyl chloride

D-glucal

N,O-bis(tertbutyldimethylsilyl)acetamide

t-butyldimethylsiyl triflate

Downstream raw materials:

3,4-di-O-acetyl-1,5-anhydro-6-O-t-butyldimethylsilyl-2-deoxy-D-arabino-hex-1-enitol

1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol

1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-arabino-hex-1-enopyranose

Refernces

• 1、 Lv, Jian,Luo, Tao,Zou, Dapeng,Dong, Hai. "Using DMF as Both a Catalyst and Cosolvent for the Regioselective Silylation of Polyols and Diols". . p. 6383 - 6395. Retrieved 2019/11/05.
• 2、 Xiao, Mingxing,Wu, Wei,Wei, Lin,Jin, Xiaojie,Yao, Xiaojun,Xie, Zhixiang. "Total synthesis of (-)-isatisine A via a biomimetic benzilic acid rearrangement". . p. 3705 - 3714. Retrieved 2015/05/20.