(2R,3S,4R)-N-diphenylmethylene-5-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-4-aminopentane-1,2,3,5-tetraol

Base Information

Chemical Name:(2R,3S,4R)-N-diphenylmethylene-5-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-4-aminopentane-1,2,3,5-tetraol
CAS No.:208253-72-9
Molecular Formula:C₂₉H₄₃NO₅Si
Molecular Weight:513.75
Hs Code.:

Synonyms:(2R,3S,4R)-N-diphenylmethylene-5-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-4-aminopentane-1,2,3,5-tetraol

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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,3S,4R)-N-diphenylmethylene-5-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-4-aminopentane-1,2,3,5-tetraol

Chemical Property:

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Technology Process of (2R,3S,4R)-N-diphenylmethylene-5-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-4-aminopentane-1,2,3,5-tetraol

There total 3 articles about (2R,3S,4R)-N-diphenylmethylene-5-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-4-aminopentane-1,2,3,5-tetraol 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: 70.0%

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

: 208253-72-9
(2R,3S,4R)-N-diphenylmethylene-5-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-4-aminopentane-1,2,3,5-tetraol

: (2S,3S,4R)-N-diphenylmethylene-5-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-4-aminopentane-1,2,3,5-tetraol

Guidance literature:: With potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; sodium hydrogencarbonate; potassium carbonate; potassium hexacyanoferrate(III); In water; tert-butyl alcohol;
DOI:10.1016/S0040-4039(98)00495-X

Reference yield:

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

: 208253-72-9
(2R,3S,4R)-N-diphenylmethylene-5-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-4-aminopentane-1,2,3,5-tetraol

Guidance literature:: Multi-step reaction with 3 steps

1: DIBAL; TRIBAl / hexane; CH₂Cl₂; tetrahydrofuran / 10 h / -78 - 20 °C

2: 92 percent / DMAP; pyridine / 60 h / 0 - 20 °C

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

With pyridine; dmap; K₂Os(OH)4; TRIBAl; diisobutylaluminium hydride; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol; 1: Addition / 2: Acylation / 3: dihydroxylation;
DOI:10.1021/jo000527u

Reference yield:

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

: 208253-72-9
(2R,3S,4R)-N-diphenylmethylene-5-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-4-aminopentane-1,2,3,5-tetraol

Guidance literature:: Multi-step reaction with 2 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

With pyridine; dmap; K₂Os(OH)4; potassium carbonate; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; 1: Acylation / 2: dihydroxylation;
DOI:10.1021/jo000527u