3,5-O-benzylidene-1-O-[tert-butyl(dimethyl)silyl]-2,4,7,8-tetradeoxy-9-O-(4-methoxybenzyl)-2,4,8-trimethyl-6-C-methyl-6-O-(triethylsilyl)-L-threo-L-ido-nonitol

Base Information

Chemical Name:3,5-O-benzylidene-1-O-[tert-butyl(dimethyl)silyl]-2,4,7,8-tetradeoxy-9-O-(4-methoxybenzyl)-2,4,8-trimethyl-6-C-methyl-6-O-(triethylsilyl)-L-threo-L-ido-nonitol
CAS No.:863663-22-3
Molecular Formula:C₄₀H₆₈O₆Si₂
Molecular Weight:701.147
Hs Code.:

3,5-O-benzylidene-1-O-[tert-butyl(dimethyl)silyl]-2,4,7,8-tetradeoxy-9-O-(4-methoxybenzyl)-2,4,8-trimethyl-6-C-methyl-6-O-(triethylsilyl)-L-threo-L-ido-nonitol

Synonyms:3,5-O-benzylidene-1-O-[tert-butyl(dimethyl)silyl]-2,4,7,8-tetradeoxy-9-O-(4-methoxybenzyl)-2,4,8-trimethyl-6-C-methyl-6-O-(triethylsilyl)-L-threo-L-ido-nonitol

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Chemical Property of 3,5-O-benzylidene-1-O-[tert-butyl(dimethyl)silyl]-2,4,7,8-tetradeoxy-9-O-(4-methoxybenzyl)-2,4,8-trimethyl-6-C-methyl-6-O-(triethylsilyl)-L-threo-L-ido-nonitol

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Technology Process of 3,5-O-benzylidene-1-O-[tert-butyl(dimethyl)silyl]-2,4,7,8-tetradeoxy-9-O-(4-methoxybenzyl)-2,4,8-trimethyl-6-C-methyl-6-O-(triethylsilyl)-L-threo-L-ido-nonitol

There total 9 articles about 3,5-O-benzylidene-1-O-[tert-butyl(dimethyl)silyl]-2,4,7,8-tetradeoxy-9-O-(4-methoxybenzyl)-2,4,8-trimethyl-6-C-methyl-6-O-(triethylsilyl)-L-threo-L-ido-nonitol 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: 87.0%

: 863663-32-5
9-O-[tert-butyl(dimethyl)silyl]-2,3,6,8-tetradeoxy-1-O-(4-methoxybenzyl)-2,6,8-trimethyl-4-C-methyl-4-O-(triethylsilyl)-L-threo-L-ido-nonitol

: 1125-88-8
benzaldehyde dimethyl acetal

: 863663-22-3
3,5-O-benzylidene-1-O-[tert-butyl(dimethyl)silyl]-2,4,7,8-tetradeoxy-9-O-(4-methoxybenzyl)-2,4,8-trimethyl-6-C-methyl-6-O-(triethylsilyl)-L-threo-L-ido-nonitol

Guidance literature:: With camphor-10-sulfonic acid; In toluene; at 20 ℃; for 1.5h; under 7.5006 Torr;
DOI:10.1002/anie.200500172

Reference yield:

: C₁₀H₂₂ClNO₂Si

: 863663-22-3
3,5-O-benzylidene-1-O-[tert-butyl(dimethyl)silyl]-2,4,7,8-tetradeoxy-9-O-(4-methoxybenzyl)-2,4,8-trimethyl-6-C-methyl-6-O-(triethylsilyl)-L-threo-L-ido-nonitol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.20 g / EtMgBr / CH₂Cl₂; diethyl ether; propan-2-ol / 0 - 20 °C

2: 82 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

3: 64 percent / t-BuLi; MgBr₂ / diethyl ether; pentane; various solvents / 1 h / -78 °C

4: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

5: 89 percent / Raney-Ni; boric acid; H₂ / methanol; H₂O / 2 h / 20 °C

6: 60 percent / Zn(BH₄)2 / diethyl ether; CH₂Cl₂ / -78 - -30 °C

7: 87 percent / CSA / toluene / 1.5 h / 20 °C / 7.5 Torr

With 2,6-dimethylpyridine; N-methyl-2-indolinone; tetrapropylammonium perruthennate; zinc(II) tetrahydroborate; 4 A molecular sieve; camphor-10-sulfonic acid; ethylmagnesium bromide; hydrogen; tert.-butyl lithium; boric acid; nickel; magnesium bromide; In methanol; diethyl ether; dichloromethane; various solvents; water; isopropyl alcohol; toluene; pentane;
DOI:10.1002/anie.200500172

Reference yield:

: C₁₂H₁₇BrMgO₂

: 863663-22-3
3,5-O-benzylidene-1-O-[tert-butyl(dimethyl)silyl]-2,4,7,8-tetradeoxy-9-O-(4-methoxybenzyl)-2,4,8-trimethyl-6-C-methyl-6-O-(triethylsilyl)-L-threo-L-ido-nonitol

Guidance literature:: Multi-step reaction with 5 steps

1: 64 percent / t-BuLi; MgBr₂ / diethyl ether; pentane; various solvents / 1 h / -78 °C

2: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

3: 89 percent / Raney-Ni; boric acid; H₂ / methanol; H₂O / 2 h / 20 °C

4: 60 percent / Zn(BH₄)2 / diethyl ether; CH₂Cl₂ / -78 - -30 °C

5: 87 percent / CSA / toluene / 1.5 h / 20 °C / 7.5 Torr

With 2,6-dimethylpyridine; zinc(II) tetrahydroborate; camphor-10-sulfonic acid; hydrogen; tert.-butyl lithium; boric acid; nickel; magnesium bromide; In methanol; diethyl ether; dichloromethane; various solvents; water; toluene; pentane;
DOI:10.1002/anie.200500172