2-[(2S,3S,6R)-3-benzyloxy-6-((S)-6-hydroxyhept-1(Z)-enyl)tetrahydro-2H-pyran-2-yl]acetic acid

Base Information

Chemical Name:2-[(2S,3S,6R)-3-benzyloxy-6-((S)-6-hydroxyhept-1(Z)-enyl)tetrahydro-2H-pyran-2-yl]acetic acid
CAS No.:1372785-77-7
Molecular Formula:C₂₁H₃₀O₅
Molecular Weight:362.466
Hs Code.:

Synonyms:2-[(2S,3S,6R)-3-benzyloxy-6-((S)-6-hydroxyhept-1(Z)-enyl)tetrahydro-2H-pyran-2-yl]acetic acid

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Chemical Property of 2-[(2S,3S,6R)-3-benzyloxy-6-((S)-6-hydroxyhept-1(Z)-enyl)tetrahydro-2H-pyran-2-yl]acetic acid

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Technology Process of 2-[(2S,3S,6R)-3-benzyloxy-6-((S)-6-hydroxyhept-1(Z)-enyl)tetrahydro-2H-pyran-2-yl]acetic acid

There total 20 articles about 2-[(2S,3S,6R)-3-benzyloxy-6-((S)-6-hydroxyhept-1(Z)-enyl)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: 25.0%

: 1372785-49-3
2-((2S,3S,6R)-3-(benzyloxy)-6-vinyl-tetrahydro-2H-pyran-2-yl)acetic acid

: 88980-13-6
(S)-hept-6-en-2-ol

: 1372785-77-7
2-[(2S,3S,6R)-3-benzyloxy-6-((S)-6-hydroxyhept-1(Z)-enyl)tetrahydro-2H-pyran-2-yl]acetic acid

: 1173181-30-0
2-[(2S,3S,6R)-3-benzyloxy-6-((S)-6-hydroxyhept-1(E)-enyl)tetrahydro-2H-pyran-2-yl]acetic acid

: 1372785-48-2
(2S,11S,E)-dodec-6-ene-2,11-diol

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 2h; optical yield given as %de; Inert atmosphere; Reflux;
DOI:10.1016/j.tetasy.2012.02.009

Reference yield:

: 2-[(2S,3S,6R)-3-benzyloxy-6-(prop-1-enyl)tetrahydro-2H-pyran-2-yl]acetic acid

: 88980-13-6
(S)-hept-6-en-2-ol

: 1372785-77-7
2-[(2S,3S,6R)-3-benzyloxy-6-((S)-6-hydroxyhept-1(Z)-enyl)tetrahydro-2H-pyran-2-yl]acetic acid

: 1173181-30-0
2-[(2S,3S,6R)-3-benzyloxy-6-((S)-6-hydroxyhept-1(E)-enyl)tetrahydro-2H-pyran-2-yl]acetic acid

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 6h; optical yield given as %de; Heating;
DOI:10.1016/j.tetlet.2009.04.026

Reference yield:

: 1372785-52-8
(S)-4-((S)-1-(4-methoxybenzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane

: 1372785-77-7
2-[(2S,3S,6R)-3-benzyloxy-6-((S)-6-hydroxyhept-1(Z)-enyl)tetrahydro-2H-pyran-2-yl]acetic acid

: 1173181-30-0
2-[(2S,3S,6R)-3-benzyloxy-6-((S)-6-hydroxyhept-1(E)-enyl)tetrahydro-2H-pyran-2-yl]acetic acid

: 1372785-48-2
(2S,11S,E)-dodec-6-ene-2,11-diol

Guidance literature:: Multi-step reaction with 18 steps

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

1.2: -78 °C

2.1: sodium tetrahydroborate / methanol / 0 - 20 °C

3.1: 1H-imidazole / dichloromethane / 0 - 20 °C

4.1: copper(II) choride dihydrate / acetonitrile / 0 - 20 °C

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

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

7.1: magnesium / diethyl ether

7.2: 2 h / -40 - 20 °C

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

8.2: 5 h / 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 - -10 °C / Molecular sieve

13.2: 3 h / -20 - 20 °C

14.1: sodium periodate / water; acetone / 0 - 20 °C

15.1: tetrahydrofuran / 2 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: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / Inert atmosphere; Reflux

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) isopropylate; sodium tetrahydroborate; sodium periodate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(II) choride dihydrate; L-(+)-diisopropyl tartrate; [bis(acetoxy)iodo]benzene; Cumene hydroperoxide; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; ozone; magnesium; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; acetonitrile; paraffin oil; benzene; 10.1: Wittig reaction / 13.1: Sharpless asymmetric epoxidation;
DOI:10.1016/j.tetasy.2012.02.009