(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-3,4-Dihydroxy-5-methyl-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Base Information

Chemical Name:(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-3,4-Dihydroxy-5-methyl-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester
CAS No.:185200-98-0
Molecular Formula:C₃₄H₅₂O₁₃
Molecular Weight:668.779
Hs Code.:

(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-3,4-Dihydroxy-5-methyl-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Synonyms:(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-3,4-Dihydroxy-5-methyl-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

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Chemical Property of (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-3,4-Dihydroxy-5-methyl-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

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Technology Process of (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-3,4-Dihydroxy-5-methyl-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

There total 14 articles about (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-3,4-Dihydroxy-5-methyl-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl 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: 89.0%

: 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

: 185200-98-0
(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-3,4-Dihydroxy-5-methyl-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.1h;
DOI:10.1021/jo961533m

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

: 185200-98-0
(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-3,4-Dihydroxy-5-methyl-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 89 percent / NaBH₄ / methanol / 0.1 h / 0 °C

With sodium tetrahydroborate; 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

: 185200-98-0
(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-3,4-Dihydroxy-5-methyl-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Guidance literature:: Multi-step reaction with 6 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

6: 89 percent / NaBH₄ / methanol / 0.1 h / 0 °C

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