(1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tri(acetoxy)-6′-acetoxymethyl-5-chloro-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-[2H]pyran]

Base Information

Chemical Name:(1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tri(acetoxy)-6′-acetoxymethyl-5-chloro-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-[2H]pyran]
CAS No.:1005142-67-5
Molecular Formula:C₃₀H₃₃ClO₁₀
Molecular Weight:589.039
Hs Code.:

Synonyms:(1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tri(acetoxy)-6′-acetoxymethyl-5-chloro-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-[2H]pyran]

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Chemical Property of (1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tri(acetoxy)-6′-acetoxymethyl-5-chloro-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-[2H]pyran]

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Technology Process of (1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tri(acetoxy)-6′-acetoxymethyl-5-chloro-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-[2H]pyran]

There total 4 articles about (1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tri(acetoxy)-6′-acetoxymethyl-5-chloro-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-[2H]pyran] 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: 69.1%

: 1005142-65-3
(1S,3'R,4'S,5'R,6'R)-3',4',5'-tri(acetoxy)-6'-acetoxymethyl-5-chloro-6-chloromethyl-3',4',5',6'-tetrahydro-spiro[isobenzofuran-1(3H),2'-[2H]pyran]

: 63139-21-9
4-ethylphenylboronic acid

: 1005142-67-5
(1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tri(acetoxy)-6′-acetoxymethyl-5-chloro-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-[2H]pyran]

Guidance literature:: With tetrabutylammomium bromide; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In water; N,N-dimethyl-formamide; at 85 ℃; for 15h;

Reference yield:

: (1S,3'R,4'S,5'S,6'R)-5-chloro-6-[(4-ethylphenyl)methyl]-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triol

: 108-24-7
acetic anhydride

: 1005142-67-5
(1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tri(acetoxy)-6′-acetoxymethyl-5-chloro-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-[2H]pyran]

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 10h;
DOI:10.1007/s00706-015-1458-z

Reference yield:

: 85072-44-2
1-bromo-4-chloro-2,5-dimethylbenzene

: 1005142-67-5
(1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tri(acetoxy)-6′-acetoxymethyl-5-chloro-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-[2H]pyran]

Guidance literature:: Multi-step reaction with 8 steps

1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / ethyl acetate / 0.33 h / Reflux

2.1: N,N-dimethyl-formamide / 3 h / 80 °C

3.1: potassium hydroxide; water / tetrahydrofuran; ethanol / 3 h / 80 °C

4.1: pyridinium p-toluenesulfonate / tetrahydrofuran / 2 h / 0 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.42 h / -78 °C / Inert atmosphere

5.2: 0.08 h

6.1: toluene-4-sulfonic acid / tetrahydrofuran; methanol / 15 h / 20 °C

7.1: chloro-trimethyl-silane / dimethyl sulfoxide / 4 h / 20 °C

7.2: 1 h / 0 - 20 °C

8.1: tetrabutylammomium bromide; bis(cyclopentadienyl)titanium dichloride; sodium carbonate / water; N,N-dimethyl-formamide / 15 h / 85 °C

With bis(cyclopentadienyl)titanium dichloride; N-Bromosuccinimide; n-butyllithium; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); tetrabutylammomium bromide; water; pyridinium p-toluenesulfonate; sodium carbonate; toluene-4-sulfonic acid; potassium hydroxide; In tetrahydrofuran; methanol; ethanol; hexane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm300884k