2-((2R,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran 2-yl)acetic acid

Base Information

Chemical Name:2-((2R,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran 2-yl)acetic acid
CAS No.:1372785-66-4
Molecular Formula:C₁₆H₂₀O₄
Molecular Weight:276.332
Hs Code.:

Synonyms:2-((2R,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran 2-yl)acetic acid

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Chemical Property of 2-((2R,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran 2-yl)acetic acid

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Technology Process of 2-((2R,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran 2-yl)acetic acid

There total 19 articles about 2-((2R,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran 2-yl)acetic acid 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: 75.0%

: 1372785-76-6
2-((2R,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran-2-yl)ethanol

: 1372785-66-4
2-((2R,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran 2-yl)acetic acid

Guidance literature:: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; water; at 0 ℃; for 1h;
DOI:10.1016/j.tetasy.2012.02.009

Reference yield:

: 1372785-69-7
(3R,4S)-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)oct-7-en-3-yl 4-nitrobenzoate

: 1372785-66-4
2-((2R,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran 2-yl)acetic acid

Guidance literature:: Multi-step reaction with 11 steps

1.1: methanol; potassium carbonate / 2 h / 20 °C

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

2.2: 5 h / 0 - 20 °C

3.1: ozone / dichloromethane / 0.25 h / -78 °C

3.2: -78 °C

4.1: benzene / 2 h / Reflux

5.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / 0 °C

5.2: 1 h / 20 °C

6.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C

7.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; Cumene hydroperoxide / dichloromethane / 6 h / -20 °C / Molecular sieve

7.2: 3 h / -20 - 20 °C

8.1: sodium periodate / water; acetone / 0.5 h / 20 °C

9.1: tetrahydrofuran / 1 h / 20 °C

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

11.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 1 h / 0 °C

With titanium(IV) isopropylate; methanol; sodium periodate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; L-(+)-diisopropyl tartrate; [bis(acetoxy)iodo]benzene; Cumene hydroperoxide; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water; acetone; benzene; 4.1: Wittig reaction / 7.1: Sharpless asymmetric epoxidation / 9.1: Wittig reaction;
DOI:10.1016/j.tetasy.2012.02.009

Reference yield:

: 1372785-54-0
(2S,3S)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)pentane-1,2-diol

: 1372785-66-4
2-((2R,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran 2-yl)acetic acid

Guidance literature:: Multi-step reaction with 17 steps

1.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0.5 h / 20 °C

2.1: potassium carbonate / methanol / 1 h / 20 °C

3.1: magnesium / diethyl ether

3.2: 2 h / -40 - 20 °C

4.1: sodium hydride / tetrahydrofuran; paraffin oil / 0.5 h / 0 °C

4.2: 5 h / 20 °C

5.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C

6.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

7.1: methanol; potassium carbonate / 2 h / 20 °C

8.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

8.2: 5 h / 0 - 20 °C

9.1: ozone / dichloromethane / 0.25 h / -78 °C

9.2: -78 °C

10.1: benzene / 2 h / Reflux

11.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / 0 °C

11.2: 1 h / 20 °C

12.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C

13.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; Cumene hydroperoxide / dichloromethane / 6 h / -20 °C / Molecular sieve

13.2: 3 h / -20 - 20 °C

14.1: sodium periodate / water; acetone / 0.5 h / 20 °C

15.1: tetrahydrofuran / 1 h / 20 °C

16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

17.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 1 h / 0 °C

With titanium(IV) isopropylate; methanol; sodium periodate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; L-(+)-diisopropyl tartrate; [bis(acetoxy)iodo]benzene; Cumene hydroperoxide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; ozone; magnesium; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; paraffin oil; benzene; 6.1: Mitsunobu reaction / 10.1: Wittig reaction / 13.1: Sharpless asymmetric epoxidation / 15.1: Wittig reaction;
DOI:10.1016/j.tetasy.2012.02.009