{(2R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester

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Chemical Name:{(2R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester
CAS No.:288591-15-1
Molecular Formula:C₂₀H₃₂O₄Si
Molecular Weight:364.557
Hs Code.:

Synonyms:{(2R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester

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Chemical Property of {(2R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester

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Technology Process of {(2R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester

There total 10 articles about {(2R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester 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: 92.0%

: 288591-14-0
(E)-(S)-7-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-7-hydroxy-hept-2-enoic acid methyl ester

: 288591-15-1
{(2R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0960-894X(00)00230-4

Reference yield:

: 2398-37-0
3-methoxyphenyl bromide

: 288591-15-1
{(2R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: Mg / tetrahydrofuran / 20 °C

2: aq. HCl

3: 100 percent / pyridinium hydrochloride / 150 °C

4: 94 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

5: 72 percent / N-methylmorpholine oxide; OsO₄ / acetone; H₂O / 20 °C

6: 97 percent / sodium metaperiodate / tetrahydrofuran; H₂O / 20 °C

7: tetrahydrofuran / 20 °C

8: 56 percent / (-)-diisopinocampheyl-chloroborane / tetrahydrofuran / -25 °C

9: 92 percent / NaH / tetrahydrofuran / 20 °C

With hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; pyridine hydrochloride; sodium hydride; magnesium; 4-methylmorpholine N-oxide; triethylamine; (-)-diisopinocamphenylborane chloride; In tetrahydrofuran; dichloromethane; water; acetone; 1: Grignard reaction / 2: Dehydration / 3: Demethylation / 4: Silylation / 5: Dihydroxylation / 6: Oxidation / 7: Condensation / 8: Reduction / 9: Cyclization;
DOI:10.1016/S0960-894X(00)00230-4

Reference yield:

: 36742-36-6
1-(3-methoxyphenyl)cyclopentene

: 288591-15-1
{(2R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / pyridinium hydrochloride / 150 °C

2: 94 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

3: 72 percent / N-methylmorpholine oxide; OsO₄ / acetone; H₂O / 20 °C

4: 97 percent / sodium metaperiodate / tetrahydrofuran; H₂O / 20 °C

5: tetrahydrofuran / 20 °C

6: 56 percent / (-)-diisopinocampheyl-chloroborane / tetrahydrofuran / -25 °C

7: 92 percent / NaH / tetrahydrofuran / 20 °C

With dmap; sodium periodate; osmium(VIII) oxide; pyridine hydrochloride; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; (-)-diisopinocamphenylborane chloride; In tetrahydrofuran; dichloromethane; water; acetone; 1: Demethylation / 2: Silylation / 3: Dihydroxylation / 4: Oxidation / 5: Condensation / 6: Reduction / 7: Cyclization;
DOI:10.1016/S0960-894X(00)00230-4