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

Base Information

Chemical Name:(1S,3'R,4'S,5'S,6'R)-6-[(4-ethylphenyl)methyl]-5-fluoro-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triol
CAS No.:1005142-15-3
Molecular Formula:C₂₂H₂₅FO₆
Molecular Weight:404.435
Hs Code.:

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

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

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

There total 9 articles about (1S,3'R,4'S,5'S,6'R)-6-[(4-ethylphenyl)methyl]-5-fluoro-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triol 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: 74.0%

: 1005142-81-3
(1S,3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-6-[(4-ethylphenyl)methyl]-5-fluoro-3',4',5',6'-tetrahydro-spiro[isobenzofuran-1(3H),2'-[2H]pyran]

: 1005142-15-3
(1S,3'R,4'S,5'S,6'R)-6-[(4-ethylphenyl)methyl]-5-fluoro-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triol

Guidance literature:: With hydrogenchloride; hydrogen; palladium 10% on activated carbon; In methanol; water; ethyl acetate; for 2h;

Reference yield: 74.0%

: (1S,3'R,4'S,5'S,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-6-[(4-ethylphenyl)methyl]-5-fluoro-3',4',5',6'-tetrahydro-spiro[isobenzofuran-1(3H),2'-[2H]pyran]

: 1005142-15-3
(1S,3'R,4'S,5'S,6'R)-6-[(4-ethylphenyl)methyl]-5-fluoro-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triol

Guidance literature:: With hydrogenchloride; hydrogen; palladium 10% on activated carbon; In methanol; water; ethyl acetate; for 2h;

Reference yield:

: 202865-66-5
2-bromo-5-fluorobenzyl alcohol

: 1005142-15-3
(1S,3'R,4'S,5'S,6'R)-6-[(4-ethylphenyl)methyl]-5-fluoro-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 - 40 °C

1.2: 0.5 h / -78 - 20 °C

2.1: sodium tetrahydroborate / methanol / 0.17 h / 0 °C

3.1: toluene-4-sulfonic acid / tetrahydrofuran / 0.67 h / 0 °C

4.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

4.2: 0.83 h / -78 °C

5.1: triphenylphosphine; tetrachloromethane / dichloromethane / 1.5 h / 20 °C

6.1: sodium carbonate; tetrabutylammomium bromide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; water / 0.33 h / 140 °C / Microwave irradiation

7.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethyl acetate; water; methanol / 2 h

With 2,2,6,6-tetramethyl-piperidine; hydrogenchloride; tetrachloromethane; sodium tetrahydroborate; n-butyllithium; tetrabutylammomium bromide; hydrogen; sodium carbonate; toluene-4-sulfonic acid; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;