(2R,3R)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-amino-4-pentene-1,2-diol

Base Information

Chemical Name:(2R,3R)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-amino-4-pentene-1,2-diol
CAS No.:208253-70-7
Molecular Formula:C₂₄H₃₃NO₂Si
Molecular Weight:395.617
Hs Code.:

Synonyms:(2R,3R)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-amino-4-pentene-1,2-diol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-amino-4-pentene-1,2-diol

Chemical Property:

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Technology Process of (2R,3R)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-amino-4-pentene-1,2-diol

There total 1 articles about (2R,3R)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-amino-4-pentene-1,2-diol 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:

: 1826-67-1
vinyl magnesium bromide

: 208253-69-4
(R)-2-(Benzhydrylidene-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester

: 208253-70-7
(2R,3R)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-amino-4-pentene-1,2-diol

: (2R,3S)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-amino-4-pentene-1,2-diol

Guidance literature:: With i-Bu₂AlH*i-Bu₃Al; Yield given. Multistep reaction. Yields of byproduct given; 2.) -78 deg C to r.t.;
DOI:10.1016/S0040-4039(98)00495-X

Reference yield: 92.0%

: 3282-30-2
pivaloyl chloride

: 208253-70-7
(2R,3R)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-amino-4-pentene-1,2-diol

: 208253-71-8
(2R,3R)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-2-amino-4-pentene-1,2-diol

Guidance literature:: With pyridine; dmap;
DOI:10.1016/S0040-4039(98)00495-X

Reference yield:

: 208253-70-7
(2R,3R)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-amino-4-pentene-1,2-diol

: 301523-19-3
5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-N-diphenylmethyl-1,4,6,7-tetradeoxy-1,4-imino-D-gulo-octitol

Guidance literature:: Multi-step reaction with 10 steps

1: 92 percent / DMAP; pyridine / 60 h / 0 - 20 °C

2: K₂Os(OH)4; K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 20 °C / pH 12

3: 84 percent / LiBH₄ / tetrahydrofuran / Heating

4: 90 percent / PPh₃; CCl₄; Et₃N / dimethylformamide / 17 h / 20 °C

5: 81 percent / CSA / CH₂Cl₂ / 72 h / Heating

6: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

7: 66 percent / methanol / 96 h / 20 °C

8: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

9: tetrahydrofuran / 20 h / 20 °C

10: 57.2 mg / NaOH; aq. H₂O₂ / tetrahydrofuran; ethanol / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; tetrachloromethane; dmap; sodium hydroxide; lithium borohydride; oxalyl dichloride; K₂Os(OH)4; camphor-10-sulfonic acid; dihydrogen peroxide; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Acylation / 2: dihydroxylation / 3: Reduction / 4: cyclocondensation / 5: ether cleavage, cyclocondensation / 6: Oxidation / 7: Addition / 8: Condensation / 9: Addition / 10: Oxidation;
DOI:10.1021/jo000527u