[(2R,3S,6R)-3-Hydroxy-6-((1R,6S)-1,6,8-tris-benzyloxy-octyl)-tetrahydro-pyran-2-yl]-acetic acid

Base Information

Chemical Name:[(2R,3S,6R)-3-Hydroxy-6-((1R,6S)-1,6,8-tris-benzyloxy-octyl)-tetrahydro-pyran-2-yl]-acetic acid
CAS No.:528598-50-7
Molecular Formula:C₃₆H₄₆O₇
Molecular Weight:590.757
Hs Code.:

Synonyms:[(2R,3S,6R)-3-Hydroxy-6-((1R,6S)-1,6,8-tris-benzyloxy-octyl)-tetrahydro-pyran-2-yl]-acetic acid

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Chemical Property of [(2R,3S,6R)-3-Hydroxy-6-((1R,6S)-1,6,8-tris-benzyloxy-octyl)-tetrahydro-pyran-2-yl]-acetic acid

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Technology Process of [(2R,3S,6R)-3-Hydroxy-6-((1R,6S)-1,6,8-tris-benzyloxy-octyl)-tetrahydro-pyran-2-yl]-acetic acid

There total 15 articles about [(2R,3S,6R)-3-Hydroxy-6-((1R,6S)-1,6,8-tris-benzyloxy-octyl)-tetrahydro-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: 97.0%

: 528598-48-3
[(2R,3S,6R)-3-Hydroxy-6-((1R,6S)-1,6,8-tris-benzyloxy-octyl)-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

: 528598-50-7
[(2R,3S,6R)-3-Hydroxy-6-((1R,6S)-1,6,8-tris-benzyloxy-octyl)-tetrahydro-pyran-2-yl]-acetic acid

Guidance literature:: With sodium hydroxide; In ethanol; at 20 ℃;
DOI:10.1021/ol034323m

Reference yield:

: 115114-87-9
(2R)-2-(2-benzyloxyethyl)oxirane

: 528598-50-7
[(2R,3S,6R)-3-Hydroxy-6-((1R,6S)-1,6,8-tris-benzyloxy-octyl)-tetrahydro-pyran-2-yl]-acetic acid

Guidance literature:: Multi-step reaction with 15 steps

1.1: BF₃*Et₂O / tetrahydrofuran / -78 °C

2.1: K₂CO₃; MeOH / 20 °C

3.1: 99 percent / NaH; n-Bu₄NI / dimethylformamide / 0 °C

4.1: n-BuLi / tetrahydrofuran

4.2: N,N-dimethylpropyleneurea / tetrahydrofuran / -15 °C

5.1: TBAF / tetrahydrofuran / 20 °C

6.1: 95 percent / H₂ / (Ph₃P)3RhCl / benzene / 20 °C

7.1: Et₃N / CH₂Cl₂ / -15 °C

8.1: CuBr / diethyl ether / -15 - 20 °C

9.1: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

9.2: 76 percent / CSA / methanol / 0 °C

10.1: 98 percent / NaH; Bu₄NI / dimethylformamide / 0 - 20 °C

11.1: 97 percent / Zn(OTf)2 / 1,2-dichloro-ethane / 50 °C

12.1: 94 percent / N-methylmorpholine / CH₂Cl₂ / 20 °C

13.1: 92 percent / MeI; aq. NaHCO₃ / acetonitrile / 0 - 20 °C

14.1: 95 percent / SmI₂ / methanol; tetrahydrofuran / 0 °C

15.1: 97 percent / aq. NaOH / ethanol / 20 °C

With 4-methyl-morpholine; methanol; sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; samarium diiodide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; copper(I) bromide; methyl iodide; Wilkinson's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ol034323m

Reference yield:

: (S)-1-Benzyloxy-hex-5-yn-3-ol

: 528598-50-7
[(2R,3S,6R)-3-Hydroxy-6-((1R,6S)-1,6,8-tris-benzyloxy-octyl)-tetrahydro-pyran-2-yl]-acetic acid

Guidance literature:: Multi-step reaction with 13 steps

1.1: 99 percent / NaH; n-Bu₄NI / dimethylformamide / 0 °C

2.1: n-BuLi / tetrahydrofuran

2.2: N,N-dimethylpropyleneurea / tetrahydrofuran / -15 °C

3.1: TBAF / tetrahydrofuran / 20 °C

4.1: 95 percent / H₂ / (Ph₃P)3RhCl / benzene / 20 °C

5.1: Et₃N / CH₂Cl₂ / -15 °C

6.1: CuBr / diethyl ether / -15 - 20 °C

7.1: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

7.2: 76 percent / CSA / methanol / 0 °C

8.1: 98 percent / NaH; Bu₄NI / dimethylformamide / 0 - 20 °C

9.1: 97 percent / Zn(OTf)2 / 1,2-dichloro-ethane / 50 °C

10.1: 94 percent / N-methylmorpholine / CH₂Cl₂ / 20 °C

11.1: 92 percent / MeI; aq. NaHCO₃ / acetonitrile / 0 - 20 °C

12.1: 95 percent / SmI₂ / methanol; tetrahydrofuran / 0 °C

13.1: 97 percent / aq. NaOH / ethanol / 20 °C

With 4-methyl-morpholine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; samarium diiodide; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; triethylamine; copper(I) bromide; methyl iodide; Wilkinson's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ol034323m