4-O-benzyl-6-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-threo-hex-2-eno-1,5-aldonolactone

Base Information

Chemical Name:4-O-benzyl-6-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-threo-hex-2-eno-1,5-aldonolactone
CAS No.:186598-60-7
Molecular Formula:C₂₉H₃₂O₄Si
Molecular Weight:472.656
Hs Code.:

Synonyms:4-O-benzyl-6-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-threo-hex-2-eno-1,5-aldonolactone

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Chemical Property of 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-threo-hex-2-eno-1,5-aldonolactone

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Technology Process of 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-threo-hex-2-eno-1,5-aldonolactone

There total 9 articles about 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-threo-hex-2-eno-1,5-aldonolactone 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: 98.0%

: 617673-22-0
Benzoic acid (2R,3R,4R)-3-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-oxo-tetrahydro-pyran-4-yl ester

: 186598-60-7
4-O-benzyl-6-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-threo-hex-2-eno-1,5-aldonolactone

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/S0040-4020(03)00873-1

Reference yield:

: 124648-31-3
6-((tert-butyldimethylsilyl)oxy)-3-O-benzoyl-D-galactal

: 186598-60-7
4-O-benzyl-6-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-threo-hex-2-eno-1,5-aldonolactone

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / NaH / dimethylformamide / 6 h / 0 °C

2: 95 percent / TBAG / tetrahydrofuran / 3 h / 20 °C

3: 100 percent / imidazole / dimethylformamide / 2 h / 20 °C

4: 51 percent / PCC / 1,2-dichloro-ethane / 6 h / 80 °C

5: 98 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(03)00873-1

Reference yield:

: 124751-19-5
(2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

: 186598-60-7
4-O-benzyl-6-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-threo-hex-2-eno-1,5-aldonolactone

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / pyridine / -35 - 0 °C

2: 92 percent / NaH / dimethylformamide / 6 h / 0 °C

3: 95 percent / TBAG / tetrahydrofuran / 3 h / 20 °C

4: 100 percent / imidazole / dimethylformamide / 2 h / 20 °C

5: 51 percent / PCC / 1,2-dichloro-ethane / 6 h / 80 °C

6: 98 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

With pyridine; 1H-imidazole; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(03)00873-1