3,6-Di-O-tert-butyldimethylsilyl-D-glucal

Base Information

• Chemical Name: 3,6-Di-O-tert-butyldimethylsilyl-D-glucal
• CAS No.: 111830-53-6
• Molecular Formula: C18H38 O4 Si2
• Molecular Weight: 374.668
• DSSTox Substance ID: DTXSID80557007
• Nikkaji Number: J2.707.736F
• Wikidata: Q82438750
• Mol file: 111830-53-6.mol

Synonyms:111830-53-6;3,6-Di-O-tert-butyldimethylsilyl-D-glucal;(2R,3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-3-ol;(2R,3R,4R)-4-((tert-Butyldimethylsilyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol;DTXSID80557007;AKOS015916594;V10114;1,5-Anhydro-3,6-bis-O-[tert-butyl(dimethyl)silyl]-2-deoxy-D-arabino-hex-1-enitol

Chemical Property of 3,6-Di-O-tert-butyldimethylsilyl-D-glucal

Chemical Property:

• Melting Point: 43-45 °C(lit.)
• Flash Point: >230 °F
• PSA: 47.92000
• LogP: 4.67200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 374.23086276
• Heavy Atom Count: 24
• Complexity: 447

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3,6-Di-O-tert-butyldimethylsilyl-D-glucal

There total 9 articles about 3,6-Di-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: 96.0%

tert-butyldimethylsilyl-2-methylprop-2-ene-1-sulfinate + D-glucal (13265-84-4) → 1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose (111830-53-6)

Guidance literature:

In d₇-N,N-dimethylformamide; regioselective reaction;

DOI:10.1002/chem.201504380

Reference yield: 90.0%

tert-butyldimethylsilyl chloride (18162-48-6) + D-glucal (13265-84-4) → tri-O-(tert-butyldimethylsilyl)-D-glucal (79999-47-6) + 1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose (111830-53-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(00)96025-8

Reference yield: 83.0%

tert-butyldimethylsilyl chloride (18162-48-6) + D-glucal (13265-84-4) → 1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose (111830-53-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 4h;

DOI:10.1002/anie.201403543

upstream raw materials:

tert-butyldimethylsilyl chloride

D-glucal

t-butyldimethylsiyl triflate

D-glucal triacetate

Downstream raw materials:

3,6-O-di-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-D-glucal

methyl 2,3,4-tri-O-benzyl-6-O-(4-O-benzyl-2-deoxy-3,6-di-O-tert-butyldimethylsilyl-β-D-erythro-hexapyranosyl)-α-D-glucopyranoside

2,2-Dimethyl-propionic acid (2R,3R,4S,4aR,7R,8R,9aR)-3,4,8-tris-benzyloxy-2-benzyloxymethyl-5-oxo-3,4,4a,5,8,9a-hexahydro-2H,7H-1,6,9-trioxa-10-thia-anthracen-7-ylmethyl ester

2,2-Dimethyl-propionic acid (3R,4R,4aS,7R,8R,9aS)-3,4,8-tris-benzyloxy-5-oxo-3,4,4a,7,8,9a-hexahydro-2H,5H-1,6,9-trioxa-10-thia-anthracen-7-ylmethyl ester