(S)-hept-6-en-2-yl 2-((2R,3S,6R)-3-(benzyloxy)-6-vinyltetrahydro-2H-pyran-2-yl)-acetate

Base Information

• Chemical Name: (S)-hept-6-en-2-yl 2-((2R,3S,6R)-3-(benzyloxy)-6-vinyltetrahydro-2H-pyran-2-yl)-acetate
• CAS No.: 1372785-65-3
• Molecular Formula: C₂₃H₃₂O₄
• Molecular Weight: 372.505

Synonyms:(S)-hept-6-en-2-yl 2-((2R,3S,6R)-3-(benzyloxy)-6-vinyltetrahydro-2H-pyran-2-yl)-acetate

Chemical Property of (S)-hept-6-en-2-yl 2-((2R,3S,6R)-3-(benzyloxy)-6-vinyltetrahydro-2H-pyran-2-yl)-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-hept-6-en-2-yl 2-((2R,3S,6R)-3-(benzyloxy)-6-vinyltetrahydro-2H-pyran-2-yl)-acetate

There total 20 articles about (S)-hept-6-en-2-yl 2-((2R,3S,6R)-3-(benzyloxy)-6-vinyltetrahydro-2H-pyran-2-yl)-acetate 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: 61.0%

2-((2R,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran 2-yl)acetic acid (1372785-66-4) + (S)-hept-6-en-2-ol (88980-13-6) → (S)-hept-6-en-2-yl 2-((2R,3S,6R)-3-(benzyloxy)-6-vinyltetrahydro-2H-pyran-2-yl)-acetate (1372785-65-3)

Guidance literature:

2-((2R,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran 2-yl)acetic acid; With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

(S)-hept-6-en-2-ol; In dichloromethane; at 0 - 20 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.02.009

Reference yield:

(3R,4S)-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)oct-7-en-3-yl 4-nitrobenzoate (1372785-69-7) → (S)-hept-6-en-2-yl 2-((2R,3S,6R)-3-(benzyloxy)-6-vinyltetrahydro-2H-pyran-2-yl)-acetate (1372785-65-3)

Guidance literature:

Multi-step reaction with 12 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

12.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

12.2: 5 h / 0 - 20 °C / Inert atmosphere

With titanium(IV) isopropylate; methanol; dmap; 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; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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:

(2S,3S)-5-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)pentane-1,2-diol (1372785-54-0) → (S)-hept-6-en-2-yl 2-((2R,3S,6R)-3-(benzyloxy)-6-vinyltetrahydro-2H-pyran-2-yl)-acetate (1372785-65-3)

Guidance literature:

Multi-step reaction with 18 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

18.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

18.2: 5 h / 0 - 20 °C / Inert atmosphere

With titanium(IV) isopropylate; methanol; dmap; 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; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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

upstream raw materials:

(3S,4S)-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)oct-7-en-3-ol

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

(3R,4S)-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)oct-7-en-3-ol

((3R,4S)-4-(benzyloxy)-3-(4-methoxybenzyloxy)oct-7-enyloxy)(tert-butyl)diphenylsilane

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