(2R,3S,4R,5R)-2-hydroxy-3-methoxymethoxy-5-(3,4-dimethoxyphenyl)-4-pivaloyloxymethyltetrahydrofuran

Base Information

Chemical Name:(2R,3S,4R,5R)-2-hydroxy-3-methoxymethoxy-5-(3,4-dimethoxyphenyl)-4-pivaloyloxymethyltetrahydrofuran
CAS No.:367909-81-7
Molecular Formula:C₂₀H₃₀O₈
Molecular Weight:398.453
Hs Code.:

Synonyms:(2R,3S,4R,5R)-2-hydroxy-3-methoxymethoxy-5-(3,4-dimethoxyphenyl)-4-pivaloyloxymethyltetrahydrofuran

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Chemical Property of (2R,3S,4R,5R)-2-hydroxy-3-methoxymethoxy-5-(3,4-dimethoxyphenyl)-4-pivaloyloxymethyltetrahydrofuran

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Technology Process of (2R,3S,4R,5R)-2-hydroxy-3-methoxymethoxy-5-(3,4-dimethoxyphenyl)-4-pivaloyloxymethyltetrahydrofuran

There total 8 articles about (2R,3S,4R,5R)-2-hydroxy-3-methoxymethoxy-5-(3,4-dimethoxyphenyl)-4-pivaloyloxymethyltetrahydrofuran 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%

: 367909-86-2
(2R,3R,4R)-2,4-bis(methoxymethoxy)-4-(3,4-dimethoxyphenyl)-3-pivaloyloxymethylbutanal

: 367909-81-7
(2R,3S,4R,5R)-2-hydroxy-3-methoxymethoxy-5-(3,4-dimethoxyphenyl)-4-pivaloyloxymethyltetrahydrofuran

Guidance literature:: With pyridinium p-toluenesulfonate; In tert-butyl alcohol; for 2h; Heating;
DOI:10.1271/bbb.65.1559

Reference yield:

: 3282-30-2
pivaloyl chloride

: 367909-81-7
(2R,3S,4R,5R)-2-hydroxy-3-methoxymethoxy-5-(3,4-dimethoxyphenyl)-4-pivaloyloxymethyltetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / 1 h / 20 °C

2: 80 percent / PPTS / methanol / 3 h / Heating

3: 89 percent / NaIO₄ / methanol / 3 h / 20 °C

4: 74 percent / PPTS / 2-methyl-propan-2-ol / 2 h / Heating

With pyridine; sodium periodate; pyridinium p-toluenesulfonate; In methanol; tert-butyl alcohol;
DOI:10.1271/bbb.65.1559

Reference yield:

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 367909-81-7
(2R,3S,4R,5R)-2-hydroxy-3-methoxymethoxy-5-(3,4-dimethoxyphenyl)-4-pivaloyloxymethyltetrahydrofuran

Guidance literature:: Multi-step reaction with 7 steps

1: LDA / tetrahydrofuran / 1 h / -75 °C

2: 81 percent / (i-Pr)2NH / CH₂Cl₂ / 3 h / 20 °C

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

4: pyridine / 1 h / 20 °C

5: 80 percent / PPTS / methanol / 3 h / Heating

6: 89 percent / NaIO₄ / methanol / 3 h / 20 °C

7: 74 percent / PPTS / 2-methyl-propan-2-ol / 2 h / Heating

With pyridine; sodium periodate; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1271/bbb.65.1559