2-C-{(2R)-2-[(4S,5R)-5-acetyl-4-methyl-4,5-dihydroisoxazol-3-yl]propyl}-3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

Base Information

Chemical Name:2-C-{(2R)-2-[(4S,5R)-5-acetyl-4-methyl-4,5-dihydroisoxazol-3-yl]propyl}-3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol
CAS No.:863663-34-7
Molecular Formula:C₃₇H₆₅NO₆Si₂
Molecular Weight:676.097
Hs Code.:

2-C-{(2R)-2-[(4S,5R)-5-acetyl-4-methyl-4,5-dihydroisoxazol-3-yl]propyl}-3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

Synonyms:2-C-{(2R)-2-[(4S,5R)-5-acetyl-4-methyl-4,5-dihydroisoxazol-3-yl]propyl}-3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

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Chemical Property of 2-C-{(2R)-2-[(4S,5R)-5-acetyl-4-methyl-4,5-dihydroisoxazol-3-yl]propyl}-3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

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Technology Process of 2-C-{(2R)-2-[(4S,5R)-5-acetyl-4-methyl-4,5-dihydroisoxazol-3-yl]propyl}-3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

There total 3 articles about 2-C-{(2R)-2-[(4S,5R)-5-acetyl-4-methyl-4,5-dihydroisoxazol-3-yl]propyl}-3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol 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: 93.0%

: 863663-25-6
3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R)-1-hydroxyethyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

: 863663-34-7
2-C-{(2R)-2-[(4S,5R)-5-acetyl-4-methyl-4,5-dihydroisoxazol-3-yl]propyl}-3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; Carbonate buffer; potassium bromide; sodium hypochlorite; In dichloromethane; at 0 ℃; for 1h; pH=8.6;
DOI:10.1002/anie.200500172

Reference yield:

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

: 863663-34-7
2-C-{(2R)-2-[(4S,5R)-5-acetyl-4-methyl-4,5-dihydroisoxazol-3-yl]propyl}-3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

Guidance literature:: Multi-step reaction with 3 steps

1: t-BuOCl / CH₂Cl₂ / 1.5 h / -78 °C

2: 0.52 g / EtMgBr / CH₂Cl₂; diethyl ether; propan-2-ol / 0 - 20 °C

3: 93 percent / TEMPO; KBr; aq. carbonate buffer / NaOCl / CH₂Cl₂ / 1 h / 0 °C / pH 8.6

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; Carbonate buffer; tert-butylhypochlorite; ethylmagnesium bromide; potassium bromide; sodium hypochlorite; In diethyl ether; dichloromethane; isopropyl alcohol;
DOI:10.1002/anie.200500172

Reference yield:

: C₃₂H₅₈ClNO₅Si₂

: 863663-34-7
2-C-{(2R)-2-[(4S,5R)-5-acetyl-4-methyl-4,5-dihydroisoxazol-3-yl]propyl}-3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

Guidance literature:: Multi-step reaction with 2 steps

1: 0.52 g / EtMgBr / CH₂Cl₂; diethyl ether; propan-2-ol / 0 - 20 °C

2: 93 percent / TEMPO; KBr; aq. carbonate buffer / NaOCl / CH₂Cl₂ / 1 h / 0 °C / pH 8.6

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; Carbonate buffer; ethylmagnesium bromide; potassium bromide; sodium hypochlorite; In diethyl ether; dichloromethane; isopropyl alcohol;
DOI:10.1002/anie.200500172