(2R,3S,4R)-2-(4-benzyloxy-3-methoxyphenyl)-4-(3,4-dimethoxybenzyl)-4-hydroxy-3-hydroxymethyltetrahydrofuran

Base Information

Chemical Name:(2R,3S,4R)-2-(4-benzyloxy-3-methoxyphenyl)-4-(3,4-dimethoxybenzyl)-4-hydroxy-3-hydroxymethyltetrahydrofuran
CAS No.:865872-76-0
Molecular Formula:C₂₈H₃₂O₇
Molecular Weight:480.558
Hs Code.:

Synonyms:(2R,3S,4R)-2-(4-benzyloxy-3-methoxyphenyl)-4-(3,4-dimethoxybenzyl)-4-hydroxy-3-hydroxymethyltetrahydrofuran

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Chemical Property of (2R,3S,4R)-2-(4-benzyloxy-3-methoxyphenyl)-4-(3,4-dimethoxybenzyl)-4-hydroxy-3-hydroxymethyltetrahydrofuran

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Technology Process of (2R,3S,4R)-2-(4-benzyloxy-3-methoxyphenyl)-4-(3,4-dimethoxybenzyl)-4-hydroxy-3-hydroxymethyltetrahydrofuran

There total 14 articles about (2R,3S,4R)-2-(4-benzyloxy-3-methoxyphenyl)-4-(3,4-dimethoxybenzyl)-4-hydroxy-3-hydroxymethyltetrahydrofuran 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:

: 4-(4-benzyloxy-3-methoxy-phenyl)-2-(3,4-dimethoxy-benzyl)-3-hydroxymethyl-butane-1,2,4-triol

: 865872-76-0
(2R,3S,4R)-2-(4-benzyloxy-3-methoxyphenyl)-4-(3,4-dimethoxybenzyl)-4-hydroxy-3-hydroxymethyltetrahydrofuran

Guidance literature:: With (1S)-10-camphorsulfonic acid; In dichloromethane; at 2 ℃; for 16h;
DOI:10.1271/bbb.69.113

Reference yield:

: 865872-73-7
(3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-3-pivaloyloxymethyl-4-butanolide

: 865872-76-0
(2R,3S,4R)-2-(4-benzyloxy-3-methoxyphenyl)-4-(3,4-dimethoxybenzyl)-4-hydroxy-3-hydroxymethyltetrahydrofuran

Guidance literature:: Multi-step reaction with 6 steps

1.1: KHMDS / tetrahydrofuran; toluene / 0.25 h / -70 °C

1.2: tetrahydrofuran; toluene / 1 h / -70 °C

2.1: KHSO₄ / toluene / 0.5 h / Heating

3.1: 66 percent / OsO₄; 4-methylmorpholine N-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 16 h / 20 °C

4.1: 51 percent / CF₃COOH; triethylsilane / CH₂Cl₂ / 16 h / 20 °C

5.1: LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

6.1: 10-camphorsulfonic acid / CH₂Cl₂ / 16 h / 2 °C

With triethylsilane; potassium hydrogensulfate; osmium(VIII) oxide; lithium aluminium tetrahydride; (1S)-10-camphorsulfonic acid; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1271/bbb.69.113

Reference yield:

: 868128-07-8
2,2-dimethyl-propionic acid 2-(4-benzyloxy-3-methoxy-phenyl)-5-hydroxy-tetrahydro-furan-3-ylmethyl ester

: 865872-76-0
(2R,3S,4R)-2-(4-benzyloxy-3-methoxyphenyl)-4-(3,4-dimethoxybenzyl)-4-hydroxy-3-hydroxymethyltetrahydrofuran

Guidance literature:: Multi-step reaction with 7 steps

1.1: 82 percent / pyridinium chlorochrmoate; molecular sieves 4 Angstroem / CH₂Cl₂ / 16 h / 20 °C

2.1: KHMDS / tetrahydrofuran; toluene / 0.25 h / -70 °C

2.2: tetrahydrofuran; toluene / 1 h / -70 °C

3.1: KHSO₄ / toluene / 0.5 h / Heating

4.1: 66 percent / OsO₄; 4-methylmorpholine N-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 16 h / 20 °C

5.1: 51 percent / CF₃COOH; triethylsilane / CH₂Cl₂ / 16 h / 20 °C

6.1: LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

7.1: 10-camphorsulfonic acid / CH₂Cl₂ / 16 h / 2 °C

With triethylsilane; potassium hydrogensulfate; osmium(VIII) oxide; lithium aluminium tetrahydride; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1271/bbb.69.113