(2R,3R,4E)-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-2,3-diol

Base Information

Chemical Name:(2R,3R,4E)-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-2,3-diol
CAS No.:152386-89-5
Molecular Formula:C₃₂H₅₈O₄Si
Molecular Weight:534.896
Hs Code.:

Synonyms:(2R,3R,4E)-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-2,3-diol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,4E)-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-2,3-diol

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Technology Process of (2R,3R,4E)-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-2,3-diol

There total 8 articles about (2R,3R,4E)-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-2,3-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: 91.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 152386-88-4
(2R,3R,4E)-3-(4'-methoxybenzyloxy)-4-octadecene-1,2-diol

: 152386-89-5
(2R,3R,4E)-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-2,3-diol

Guidance literature:: With dmap; triethylamine; In dichloromethane;
DOI:10.1016/S0040-4020(01)81834-2

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 152386-89-5
(2R,3R,4E)-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-2,3-diol

Guidance literature:: Multi-step reaction with 8 steps

1: 99 percent / p-TsOH / dimethylformamide / 5 h / 50 °C / 10 Torr

2: 100 percent / NaBH₄, LiCl / 1) THF, 30 min, 2) EtOH, 24 h

3: 94 percent / BH₃*THF / tetrahydrofuran / 6 h / Heating

4: 89 percent / p-TsOH / tetrahydrofuran

5: 1) DMSO, (COCl)2, 2) NEt₃ / 1) -78 deg C, 2 h, 2) -78 deg C, 30 min

6: 1) PhLi / 1) toluene/Et₂O, 0 deg C, 20 min, 2) THF, -30 deg C, 1 h

7: 93 percent / 2percent aq. H₂SO₄ / methanol / Ambient temperature

8: 91 percent / NEt₃, DMAP / CH₂Cl₂

With dmap; sodium tetrahydroborate; borane-THF; oxalyl dichloride; sulfuric acid; toluene-4-sulfonic acid; dimethyl sulfoxide; phenyllithium; triethylamine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)81834-2

Reference yield:

: 152386-84-0
(2R,3R)-2-O-(4-methoxybenzyl)-1,2,3,4-butanetetrol

: 152386-89-5
(2R,3R,4E)-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-2,3-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / p-TsOH / tetrahydrofuran

2: 1) DMSO, (COCl)2, 2) NEt₃ / 1) -78 deg C, 2 h, 2) -78 deg C, 30 min

3: 1) PhLi / 1) toluene/Et₂O, 0 deg C, 20 min, 2) THF, -30 deg C, 1 h

4: 93 percent / 2percent aq. H₂SO₄ / methanol / Ambient temperature

5: 91 percent / NEt₃, DMAP / CH₂Cl₂

With dmap; oxalyl dichloride; sulfuric acid; toluene-4-sulfonic acid; dimethyl sulfoxide; phenyllithium; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4020(01)81834-2