(4R,5R,6S)-4-(tert-butyldimethylsiloxymethyl)-6-hydroxymethyl-5-trimethylacetoxy-2,2-diphenyltetrahydro-1,3-oxazine

Base Information

• Chemical Name: (4R,5R,6S)-4-(tert-butyldimethylsiloxymethyl)-6-hydroxymethyl-5-trimethylacetoxy-2,2-diphenyltetrahydro-1,3-oxazine
• CAS No.: 301523-24-0
• Molecular Formula: C₂₉H₄₃NO₅Si
• Molecular Weight: 513.75

Synonyms:(4R,5R,6S)-4-(tert-butyldimethylsiloxymethyl)-6-hydroxymethyl-5-trimethylacetoxy-2,2-diphenyltetrahydro-1,3-oxazine

Chemical Property of (4R,5R,6S)-4-(tert-butyldimethylsiloxymethyl)-6-hydroxymethyl-5-trimethylacetoxy-2,2-diphenyltetrahydro-1,3-oxazine

Chemical Property:

Purity/Quality:

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Technology Process of (4R,5R,6S)-4-(tert-butyldimethylsiloxymethyl)-6-hydroxymethyl-5-trimethylacetoxy-2,2-diphenyltetrahydro-1,3-oxazine

There total 1 articles about (4R,5R,6S)-4-(tert-butyldimethylsiloxymethyl)-6-hydroxymethyl-5-trimethylacetoxy-2,2-diphenyltetrahydro-1,3-oxazine 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:

(2R,3S)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-2-amino-4-pentene-1,2-diol (301523-23-9) → 2,2-Dimethyl-propionic acid (1R,2R)-2-(benzhydrylidene-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-((R)-1,2-dihydroxy-ethyl)-propyl ester + (4R,5R,6S)-4-(tert-butyldimethylsiloxymethyl)-6-hydroxymethyl-5-trimethylacetoxy-2,2-diphenyltetrahydro-1,3-oxazine (301523-24-0) + 2,2-Dimethyl-propionic acid (1R,2R,3R)-3-(benzhydrylidene-amino)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-hydroxymethyl-butyl ester

Guidance literature:

With K₂Os(OH)4; potassium carbonate; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 20 ℃; Further Variations:; Reagents; Product distribution;

DOI:10.1021/jo000527u

Reference yield: 82.0%

(4R,5R,6S)-4-(tert-butyldimethylsiloxymethyl)-6-hydroxymethyl-5-trimethylacetoxy-2,2-diphenyltetrahydro-1,3-oxazine (301523-24-0) → (2S,3R,4R)-N-diphenylmethyl-5-O-tert-butyldimethylsilyl-4-aminopentane-1,2,3,5-tetraol

Guidance literature:

With lithium borohydride; In tetrahydrofuran; for 96h; Heating;

DOI:10.1021/jo000527u

Reference yield: 76.0%

(4R,5R,6S)-4-(tert-butyldimethylsiloxymethyl)-6-hydroxymethyl-5-trimethylacetoxy-2,2-diphenyltetrahydro-1,3-oxazine (301523-24-0) → 2,2-Dimethyl-propionic acid (1R,2R)-2-(benzhydryl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1,2-dihydroxy-ethyl)-propyl ester (1053370-76-5)

Guidance literature:

With 4 A molecular sieve; sodium cyanoborohydride; acetic acid; In acetonitrile;

DOI:10.1021/jo000527u

upstream raw materials:

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

Downstream raw materials:

2,2-Dimethyl-propionic acid (1R,2R)-2-(benzhydryl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1,2-dihydroxy-ethyl)-propyl ester

2,3-O-isopropylidene-N-diphenylmethyl-1,4-dideoxy-1,4-imino-D-ribitol

5-O-tert-butyldimethylsilyl-N-diphenylmethyl-1,4-dideoxy-1,4-imino-D-ribitol

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