(2S,3R,4R/S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

Base Information

Chemical Name:(2S,3R,4R/S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran
CAS No.:473433-17-9
Molecular Formula:C₂₉H₃₄O₅Si
Molecular Weight:490.671
Hs Code.:

Synonyms:(2S,3R,4R/S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

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Chemical Property of (2S,3R,4R/S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

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Technology Process of (2S,3R,4R/S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

There total 7 articles about (2S,3R,4R/S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran 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: 83.0%

: 473433-16-8
(1S,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxymethyl-1-(3,4-methylenedioxyphenyl)-1,4-butanediol

: 473433-17-9
(2S,3R,4R/S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

Guidance literature:: With (1S)-10-camphorsulfonic acid; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1271/bbb.66.1495

Reference yield:

: 195321-29-0
(1S,2R)-1-Benzo[1,3]dioxol-5-yl-2-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-en-1-ol

: 473433-17-9
(2S,3R,4R/S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 7 steps

1.1: 4-methylmorpholine N-oxide; osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / 20 °C

2.1: 5.24 g / sodium periodate / methanol / 3 h / 20 °C

3.1: 5.22 g / Ag₂CO₃-Celite / toluene / 1 h / Heating

4.1: LHMDS / tetrahydrofuran / 0.5 h / -75 °C

4.2: 3.04 g / tetrahydrofuran / 2 h / -75 °C

5.1: 22 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 20 °C

6.1: 57 percent / sodium borohydride / ethanol / 3 h / 20 °C

7.1: 83 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; (1S)-10-camphorsulfonic acid; 4-methylmorpholine N-oxide; silver carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1271/bbb.66.1495

Reference yield:

: 473433-14-6
(3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-(3,4-methylenedioxyphenyl)-4-butanolide

: 473433-17-9
(2S,3R,4R/S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1.1: LHMDS / tetrahydrofuran / 0.5 h / -75 °C

1.2: 3.04 g / tetrahydrofuran / 2 h / -75 °C

2.1: 22 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 20 °C

3.1: 57 percent / sodium borohydride / ethanol / 3 h / 20 °C

4.1: 83 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; (1S)-10-camphorsulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1271/bbb.66.1495