[1S-(1α(4S,5R),3α,4β,5α,6α,7β)]-1-(4-hydroxy-5-methyl-3-oxo-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,4,5-tris(1,1-dimethylethyl) ester

Base Information

Chemical Name:[1S-(1α(4S,5R),3α,4β,5α,6α,7β)]-1-(4-hydroxy-5-methyl-3-oxo-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,4,5-tris(1,1-dimethylethyl) ester
CAS No.:185200-95-7
Molecular Formula:C₃₄H₅₀O₁₃
Molecular Weight:666.763
Hs Code.:

[1S-(1α(4S,5R),3α,4β,5α,6α,7β)]-1-(4-hydroxy-5-methyl-3-oxo-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,4,5-tris(1,1-dimethylethyl) ester

Synonyms:[1S-(1α(4S,5R),3α,4β,5α,6α,7β)]-1-(4-hydroxy-5-methyl-3-oxo-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,4,5-tris(1,1-dimethylethyl) ester

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Chemical Property of [1S-(1α(4S,5R),3α,4β,5α,6α,7β)]-1-(4-hydroxy-5-methyl-3-oxo-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,4,5-tris(1,1-dimethylethyl) ester

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Technology Process of [1S-(1α(4S,5R),3α,4β,5α,6α,7β)]-1-(4-hydroxy-5-methyl-3-oxo-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,4,5-tris(1,1-dimethylethyl) ester

There total 13 articles about [1S-(1α(4S,5R),3α,4β,5α,6α,7β)]-1-(4-hydroxy-5-methyl-3-oxo-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,4,5-tris(1,1-dimethylethyl) 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:

: 185201-25-6
(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4-hydroxy-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

: 185200-95-7
[1S-(1α(4S,5R),3α,4β,5α,6α,7β)]-1-(4-hydroxy-5-methyl-3-oxo-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,4,5-tris(1,1-dimethylethyl) ester

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / HF*pyridine / tetrahydrofuran / 6 h / 0 °C

2: 97 percent / HONH₂*HCl, NaOAc*3H₂O / methanol / 2.5 h / Heating

3: 81 percent / CeCl₃, EtMgBr / tetrahydrofuran / 0.33 h / -78 °C

4: 1.) O₃, 2.) Me₂S / 1.) 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C, 10 min

With cerium(III) chloride; dimethylsulfide; ethylmagnesium bromide; hydroxylamine hydrochloride; sodium acetate; pyridine hydrogenfluoride; ozone; In tetrahydrofuran; methanol;
DOI:10.1021/jo961533m

Reference yield:

: 185201-24-5
(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

: 185200-95-7
[1S-(1α(4S,5R),3α,4β,5α,6α,7β)]-1-(4-hydroxy-5-methyl-3-oxo-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,4,5-tris(1,1-dimethylethyl) ester

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

2: 87 percent / HF*pyridine / tetrahydrofuran / 6 h / 0 °C

3: 97 percent / HONH₂*HCl, NaOAc*3H₂O / methanol / 2.5 h / Heating

4: 81 percent / CeCl₃, EtMgBr / tetrahydrofuran / 0.33 h / -78 °C

5: 1.) O₃, 2.) Me₂S / 1.) 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C, 10 min

With dmap; cerium(III) chloride; dimethylsulfide; ethylmagnesium bromide; hydroxylamine hydrochloride; sodium acetate; pyridine hydrogenfluoride; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo961533m

Reference yield:

: 71432-55-8
2-tert-butyl-1,3-diisopropylisourea

: 185200-95-7
[1S-(1α(4S,5R),3α,4β,5α,6α,7β)]-1-(4-hydroxy-5-methyl-3-oxo-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,4,5-tris(1,1-dimethylethyl) ester

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / CH₂Cl₂ / 1.) reflux 2 h, 2.) room temperature, 14 h, 3.) reflux 6 h

2: 97 percent / HONH₂*HCl, NaOAc*3H₂O / methanol / 2.5 h / Heating

3: 81 percent / CeCl₃, EtMgBr / tetrahydrofuran / 0.33 h / -78 °C

4: 1.) O₃, 2.) Me₂S / 1.) 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C, 10 min

With cerium(III) chloride; dimethylsulfide; ethylmagnesium bromide; hydroxylamine hydrochloride; sodium acetate; ozone; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo961533m