(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde

Base Information

Chemical Name:(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde
CAS No.:247184-47-0
Molecular Formula:C₂₂H₃₀O₅
Molecular Weight:374.477
Hs Code.:

Synonyms:(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde

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Chemical Property of (2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde

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Technology Process of (2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde

There total 19 articles about (2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde 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: 90.0%

: 328535-14-4
{(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methanol

: 247184-47-0
(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde

Guidance literature:: With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/jo001433n

Reference yield:

: 243464-44-0
(2S)-6-benzyloxy-1-(tert-butyldiphenylsilyloxy)-hex-4-yn-2-ol

: 247184-47-0
(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1.1: 78 percent / H₂ / Pd/C / ethyl acetate / 6 h / 760.05 Torr

2.1: 75 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 22 h / 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

3.2: 87 percent / tetrahydrofuran; hexane / 0.83 h / -78 °C

4.1: 97 percent / Et₃N; 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 0.58 h / 0 °C

5.1: CuI / tetrahydrofuran; diethyl ether / -78 - -40 °C

5.2: 99 percent / tetrahydrofuran; diethyl ether / 0.42 h / -78 °C

6.1: 76 percent / TsOH*H₂O / benzene / 2.5 h / 20 °C

7.1: 84 percent / TBAF / tetrahydrofuran / 0 - 20 °C

8.1: 90 percent / 4 Angstroem molecular sieves; tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; copper(l) iodide; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; benzene;
DOI:10.1021/jo001433n

Reference yield:

: 175398-31-9
(S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxyhexanoic acid δ-lactone

: 247184-47-0
(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

1.2: 87 percent / tetrahydrofuran; hexane / 0.83 h / -78 °C

2.1: 97 percent / Et₃N; 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 0.58 h / 0 °C

3.1: CuI / tetrahydrofuran; diethyl ether / -78 - -40 °C

3.2: 99 percent / tetrahydrofuran; diethyl ether / 0.42 h / -78 °C

4.1: 76 percent / TsOH*H₂O / benzene / 2.5 h / 20 °C

5.1: 84 percent / TBAF / tetrahydrofuran / 0 - 20 °C

6.1: 90 percent / 4 Angstroem molecular sieves; tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; copper(l) iodide; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/jo001433n