(2R,3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxycarbonyl-4-(3,4-methylenedioxyphenyl)-4-butanolide

Base Information

Chemical Name:(2R,3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxycarbonyl-4-(3,4-methylenedioxyphenyl)-4-butanolide
CAS No.:473433-15-7
Molecular Formula:C₃₀H₃₂O₇Si
Molecular Weight:532.665
Hs Code.:

Synonyms:(2R,3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxycarbonyl-4-(3,4-methylenedioxyphenyl)-4-butanolide

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Chemical Property of (2R,3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxycarbonyl-4-(3,4-methylenedioxyphenyl)-4-butanolide

Chemical Property:

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Technology Process of (2R,3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxycarbonyl-4-(3,4-methylenedioxyphenyl)-4-butanolide

There total 4 articles about (2R,3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxycarbonyl-4-(3,4-methylenedioxyphenyl)-4-butanolide 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:

: 79-22-1
methyl chloroformate

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

: 473433-15-7
(2R,3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxycarbonyl-4-(3,4-methylenedioxyphenyl)-4-butanolide

Guidance literature:: (3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-4-(3,4-methylenedioxyphenyl)-4-butanolide; With lithium hexamethyldisilazane; In tetrahydrofuran; at -75 ℃; for 0.5h;

methyl chloroformate; In tetrahydrofuran; at -75 ℃; for 2h;
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

: 473433-15-7
(2R,3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxycarbonyl-4-(3,4-methylenedioxyphenyl)-4-butanolide

Guidance literature:: Multi-step reaction with 4 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

With sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; silver carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1271/bbb.66.1495

Reference yield:

: 473433-21-5
(4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-ol

: 473433-15-7
(2R,3R,4S)-3-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxycarbonyl-4-(3,4-methylenedioxyphenyl)-4-butanolide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 5.22 g / Ag₂CO₃-Celite / toluene / 1 h / Heating

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

2.2: 3.04 g / tetrahydrofuran / 2 h / -75 °C

With silver carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;
DOI:10.1271/bbb.66.1495