1-((2S,4S,6S,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one

Base Information

Chemical Name:1-((2S,4S,6S,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one
CAS No.:410077-62-2
Molecular Formula:C₂₂H₃₂O₆
Molecular Weight:392.492
Hs Code.:

Synonyms:1-((2S,4S,6S,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one

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Chemical Property of 1-((2S,4S,6S,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one

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Technology Process of 1-((2S,4S,6S,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one

There total 10 articles about 1-((2S,4S,6S,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one 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: 66.0%

: (2R,4S,8R,10S)-2-Benzyloxymethyl-10-methoxy-8-(2-methylene-butyl)-1,7-dioxa-spiro[5.5]undecan-4-ol

: 410077-62-2
1-((2S,4S,6S,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one

: 1-((2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one

Guidance literature:: (2R,4S,8R,10S)-2-Benzyloxymethyl-10-methoxy-8-(2-methylene-butyl)-1,7-dioxa-spiro[5.5]undecan-4-ol; With osmium(VIII) oxide; N-methyl-2-indolinone; In water; acetone; for 16h;

With perchloric acid; calcium perchlorate; In dichloromethane; water; acetonitrile; for 0.833333h;

With sodium periodate; In methanol; water; for 0.333333h; Further stages.;
DOI:10.1021/ol017273z

Reference yield: 13.0%

: C₂₃H₃₆O₇

: 410077-62-2
1-((2S,4S,6S,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one

: 1-((2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one

Guidance literature:: C₂₃H₃₆O₇; With perchloric acid; calcium perchlorate tetrahydrate; In dichloromethane; acetonitrile; for 0.333333h;

With sodium periodate; In methanol; water; for 0.333333h;
DOI:10.1016/j.tet.2009.04.003

Reference yield:

: 410077-58-6
(R)-1-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-4-methylene-hexan-2-ol

: 410077-62-2
1-((2S,4S,6S,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 92 percent / imidazole / tetrahydrofuran / 16 h / 45 °C

2.1: 83 percent / TFA; H₂O / CH₂Cl₂ / 1 h

3.1: tosyl imidazole; sodium hydride / tetrahydrofuran / 0 - 20 °C

4.1: t-BuLi / diethyl ether / 1 h / -45 °C

4.2: diethyl ether / -78 - -25 °C

4.3: 69 percent / HMPA / diethyl ether / 2.5 h / 20 °C

5.1: 99 percent / NaH; 15-crown-5 / tetrahydrofuran / 16 h

6.1: 94 percent / p-toluenesulfonic acid monohydrate / acetonitrile; H₂O; tetrahydrofuran / 2 h / 20 °C

7.1: 84 percent / ammonium cerium nitrate / acetonitrile; H₂O / 0.05 h / 0 °C

8.1: NMO; osmium tetraoxide / acetone; H₂O / 16 h

8.2: HClO₄; Ca(ClO₄)2*4H₂O / CH₂Cl₂; acetonitrile; H₂O / 0.83 h

8.3: 66 percent / NaIO₄ / methanol; H₂O / 0.33 h

With 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; 15-crown-5; water; tert.-butyl lithium; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; p-toluenesulfonyl imidazole; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; acetonitrile;
DOI:10.1021/ol017273z