4-O-Benzyl-3,6-DI-O-tert-butyldimethylsilyl-D-glucal

Base Information

• Chemical Name: 4-O-Benzyl-3,6-DI-O-tert-butyldimethylsilyl-D-glucal
• CAS No.: 111830-58-1
• Molecular Formula: C₂₅H₄₄O₄Si₂
• Molecular Weight: 464.793
• DSSTox Substance ID: DTXSID401110323
• Nikkaji Number: J2.707.737D
• Mol file: 111830-58-1.mol

Synonyms:4-O-BENZYL-3,6-DI-O-TERT-BUTYLDIMETHYLSILYL-D-GLUCAL;111830-58-1;tert-butyl-[[(2R,3R,4R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-phenylmethoxy-3,4-dihydro-2H-pyran-4-yl]oxy]-dimethylsilane;DTXSID401110323;AS-40562;3-O,6-O-Bis(tert-butyldimethylsilyl)-4-O-benzyl-1,2-dideoxy-1,2-didehydro-D-glucopyranose;1,5-Anhydro-2-deoxy-3,6-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-4-O-(phenylmethyl)-D-arabino-hex-1-enitol

Chemical Property of 4-O-Benzyl-3,6-DI-O-tert-butyldimethylsilyl-D-glucal

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 464.27781295
• Heavy Atom Count: 31
• Complexity: 583

Purity/Quality:

99% ^*data from raw suppliers

4-O-BENZYL-3,6-DI-O-TERT-BUTYLDIMETHYLSILYL-D-GLUCAL 95+% ^*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)OCC2=CC=CC=C2
• 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)OCC2=CC=CC=C2

Technology Process of 4-O-Benzyl-3,6-DI-O-tert-butyldimethylsilyl-D-glucal

There total 7 articles about 4-O-Benzyl-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: 92.0%

benzyl bromide (100-39-0) + 1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose (111830-53-6) → 4-O-benzyl-1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose (111830-58-1)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at -5 - 5 ℃; for 9h; Inert atmosphere;

DOI:10.1002/asia.201300362

Reference yield: 65.0%

benzyl bromide (100-39-0) + 1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose (111830-53-6) → 4-O-benzyl-1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose (111830-58-1) + 4-O-benzyl-6-O-tert-butyldimethylsilyl-D-(-)-glucal (137792-62-2)

Guidance literature:

1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 30 - 40 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil; regioselective reaction; Inert atmosphere;

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) + 4-O-benzyl-D-(-)-glucal (58871-11-7) → 4-O-benzyl-1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose (111830-58-1)

Guidance literature:

With pyridine; In dichloromethane; at -40 ℃;

DOI:10.1016/S0960-894X(02)00471-7

upstream raw materials:

benzyl bromide

1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose

t-butyldimethylsiyl triflate

4-O-benzyl-D-(-)-glucal

Downstream raw materials:

4-O-benzyl-D-(-)-glucal

C₁₉H₃₀O₄Si

C₂₃H₃₂O₅Si

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