(2R,3S)-4-((4S,5S)-5-Azido-2-phenyl-[1,3]dioxan-4-yl)-2,3-dihydroxy-butyric acid ethyl ester

Base Information

Chemical Name:(2R,3S)-4-((4S,5S)-5-Azido-2-phenyl-[1,3]dioxan-4-yl)-2,3-dihydroxy-butyric acid ethyl ester
CAS No.:749875-25-0
Molecular Formula:C₁₆H₂₁N₃O₆
Molecular Weight:351.359
Hs Code.:

Synonyms:(2R,3S)-4-((4S,5S)-5-Azido-2-phenyl-[1,3]dioxan-4-yl)-2,3-dihydroxy-butyric acid ethyl ester

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Chemical Property of (2R,3S)-4-((4S,5S)-5-Azido-2-phenyl-[1,3]dioxan-4-yl)-2,3-dihydroxy-butyric acid ethyl ester

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Technology Process of (2R,3S)-4-((4S,5S)-5-Azido-2-phenyl-[1,3]dioxan-4-yl)-2,3-dihydroxy-butyric acid ethyl ester

There total 9 articles about (2R,3S)-4-((4S,5S)-5-Azido-2-phenyl-[1,3]dioxan-4-yl)-2,3-dihydroxy-butyric acid ethyl ester 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:

: (E)-4-((4S,5S)-5-Azido-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid ethyl ester

: 749875-25-0
(2R,3S)-4-((4S,5S)-5-Azido-2-phenyl-[1,3]dioxan-4-yl)-2,3-dihydroxy-butyric acid ethyl ester

Guidance literature:: With osmium(VIII) oxide; methanesulfonamide; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; potassium carbonate; In water; tert-butyl alcohol; at 0 ℃; for 24h;
DOI:10.1016/j.tetlet.2004.05.151

Reference yield:

: 158817-21-1
(E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol

: 749875-25-0
(2R,3S)-4-((4S,5S)-5-Azido-2-phenyl-[1,3]dioxan-4-yl)-2,3-dihydroxy-butyric acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 72 percent / (-)-DIPT; t-BuOOH; Ti(OPr-i)4 / CH₂Cl₂ / 36 h / -25 °C

2.1: 89 percent / HClO₄ / dimethylsulfoxide; H₂O / 3 h / 0 °C

3.1: 65 percent / DMAP / CH₂Cl₂ / 20 °C

4.1: 83 percent / Et₃N / CH₂Cl₂ / 5 h

5.1: 78 percent / NaN₃ / dimethylformamide

6.1: 91 percent / DDQ / CH₂Cl₂ / 3 h / 20 °C

7.1: PCC; CH₃COONa / CH₂Cl₂ / 6 h / 20 °C

7.2: 83 percent / tetrahydrofuran / 24 h / 20 °C

8.1: OsO₄; K₃Fe(CN)6; CH₃SO₂NH₂ / (DHQ)2PHAL; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; osmium(VIII) oxide; sodium azide; perchloric acid; methanesulfonamide; sodium acetate; D-(-)-diisopropyl tartrate; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; potassium carbonate; In dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Sharpless asymmetric epoxidation / 8.1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2004.05.151

Reference yield:

: 146986-42-7
((2S,3S)-3-(2-(4-methoxybenzyloxy)ethyl) oxiran-2-yl)methanol

: 749875-25-0
(2R,3S)-4-((4S,5S)-5-Azido-2-phenyl-[1,3]dioxan-4-yl)-2,3-dihydroxy-butyric acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 89 percent / HClO₄ / dimethylsulfoxide; H₂O / 3 h / 0 °C

2.1: 65 percent / DMAP / CH₂Cl₂ / 20 °C

3.1: 83 percent / Et₃N / CH₂Cl₂ / 5 h

4.1: 78 percent / NaN₃ / dimethylformamide

5.1: 91 percent / DDQ / CH₂Cl₂ / 3 h / 20 °C

6.1: PCC; CH₃COONa / CH₂Cl₂ / 6 h / 20 °C

6.2: 83 percent / tetrahydrofuran / 24 h / 20 °C

7.1: OsO₄; K₃Fe(CN)6; CH₃SO₂NH₂ / (DHQ)2PHAL; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

With dmap; osmium(VIII) oxide; sodium azide; perchloric acid; methanesulfonamide; sodium acetate; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; potassium carbonate; In dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; 7.1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2004.05.151