(1R,2R,3R)-2-(2-Hydroxy-ethyl)-4-((S)-1-methyl-4-trityloxy-butyl)-5-trityloxymethyl-cyclohex-4-ene-1,3-diol

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Chemical Name:(1R,2R,3R)-2-(2-Hydroxy-ethyl)-4-((S)-1-methyl-4-trityloxy-butyl)-5-trityloxymethyl-cyclohex-4-ene-1,3-diol
CAS No.:885483-15-8
Molecular Formula:C₅₂H₅₄O₅
Molecular Weight:758.998
Hs Code.:

Synonyms:(1R,2R,3R)-2-(2-Hydroxy-ethyl)-4-((S)-1-methyl-4-trityloxy-butyl)-5-trityloxymethyl-cyclohex-4-ene-1,3-diol

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Chemical Property of (1R,2R,3R)-2-(2-Hydroxy-ethyl)-4-((S)-1-methyl-4-trityloxy-butyl)-5-trityloxymethyl-cyclohex-4-ene-1,3-diol

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Technology Process of (1R,2R,3R)-2-(2-Hydroxy-ethyl)-4-((S)-1-methyl-4-trityloxy-butyl)-5-trityloxymethyl-cyclohex-4-ene-1,3-diol

There total 7 articles about (1R,2R,3R)-2-(2-Hydroxy-ethyl)-4-((S)-1-methyl-4-trityloxy-butyl)-5-trityloxymethyl-cyclohex-4-ene-1,3-diol 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: 88.0%

: 885483-14-7
(1R,2R,3R)-2-[2-(Dimethyl-phenyl-silanyl)-ethyl]-4-((S)-1-methyl-4-trityloxy-butyl)-5-trityloxymethyl-cyclohex-4-ene-1,3-diol

: 885483-15-8
(1R,2R,3R)-2-(2-Hydroxy-ethyl)-4-((S)-1-methyl-4-trityloxy-butyl)-5-trityloxymethyl-cyclohex-4-ene-1,3-diol

Guidance literature:: (1R,2R,3R)-2-[2-(Dimethyl-phenyl-silanyl)-ethyl]-4-((S)-1-methyl-4-trityloxy-butyl)-5-trityloxymethyl-cyclohex-4-ene-1,3-diol; With 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 100 ℃; for 14h;

With potassium fluoride; dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; water; at 90 ℃; for 1.5h;
DOI:10.1002/ejoc.200500739

Reference yield:

: 76-83-5
trityl chloride

: 885483-15-8
(1R,2R,3R)-2-(2-Hydroxy-ethyl)-4-((S)-1-methyl-4-trityloxy-butyl)-5-trityloxymethyl-cyclohex-4-ene-1,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 90 percent / DMAP; pyridine / CH₂Cl₂ / 40 h / 20 °C

2.1: 97 percent / TBAF; HOAc / tetrahydrofuran / 3 h / 20 °C

3.1: TBAF; 4 Angstroem molecular sieves / tetrahydrofuran / 14 h / 100 °C

3.2: 88 percent / KF; NaHCO₃; H₂O₂ / H₂O; tetrahydrofuran; methanol / 1.5 h / 90 °C

With pyridine; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane; 3.2: modified Tamao-Fleming oxidation;
DOI:10.1002/ejoc.200500739

Reference yield:

: 828915-86-2
Formic acid (5S,8R,9S,9aR)-8-(tert-butyl-dimethyl-silanyloxy)-9-[2-(dimethyl-phenyl-silanyl)-ethyl]-5-methyl-2-oxo-2,3,4,5,7,8,9,9a-octahydro-benzo[b]oxepin-6-ylmethyl ester

: 885483-15-8
(1R,2R,3R)-2-(2-Hydroxy-ethyl)-4-((S)-1-methyl-4-trityloxy-butyl)-5-trityloxymethyl-cyclohex-4-ene-1,3-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: LiAlH₄ / diethyl ether / -10 - 0 °C

1.2: 91 percent / LiBH₄ / diethyl ether / 0 - 20 °C

2.1: 90 percent / DMAP; pyridine / CH₂Cl₂ / 40 h / 20 °C

3.1: 97 percent / TBAF; HOAc / tetrahydrofuran / 3 h / 20 °C

4.1: TBAF; 4 Angstroem molecular sieves / tetrahydrofuran / 14 h / 100 °C

4.2: 88 percent / KF; NaHCO₃; H₂O₂ / H₂O; tetrahydrofuran; methanol / 1.5 h / 90 °C

With pyridine; dmap; lithium aluminium tetrahydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; 4.2: modified Tamao-Fleming oxidation;
DOI:10.1002/ejoc.200500739