(2S,5R)-2-tert-Butyl-5-{(2S,6S,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-5-methyl-[1,3]dioxolan-4-one

Base Information

Chemical Name:(2S,5R)-2-tert-Butyl-5-{(2S,6S,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-5-methyl-[1,3]dioxolan-4-one
CAS No.:247184-54-9
Molecular Formula:C₃₀H₄₄O₇
Molecular Weight:516.675
Hs Code.:

(2S,5R)-2-tert-Butyl-5-{(2S,6S,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-5-methyl-[1,3]dioxolan-4-one

Synonyms:(2S,5R)-2-tert-Butyl-5-{(2S,6S,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-5-methyl-[1,3]dioxolan-4-one

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Chemical Property of (2S,5R)-2-tert-Butyl-5-{(2S,6S,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-5-methyl-[1,3]dioxolan-4-one

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Technology Process of (2S,5R)-2-tert-Butyl-5-{(2S,6S,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-5-methyl-[1,3]dioxolan-4-one

There total 22 articles about (2S,5R)-2-tert-Butyl-5-{(2S,6S,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-5-methyl-[1,3]dioxolan-4-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: 70.0%

: 247184-53-8
(2S,5R)-2-tert-Butyl-5-(hydroxy-{(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}-methyl)-5-methyl-[1,3]dioxolan-4-one

: 247184-54-9
(2S,5R)-2-tert-Butyl-5-{(2S,6S,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-5-methyl-[1,3]dioxolan-4-one

Guidance literature:: (2S,5R)-2-tert-Butyl-5-(hydroxy-{(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}-methyl)-5-methyl-[1,3]dioxolan-4-one; With carbon disulfide; sodium hydride; methyl iodide; In tetrahydrofuran;

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 1.5h; Further stages.;
DOI:10.1021/jo001433n

Reference yield:

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

: 247184-54-9
(2S,5R)-2-tert-Butyl-5-{(2S,6S,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-5-methyl-[1,3]dioxolan-4-one

Guidance literature:: Multi-step reaction with 10 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

9.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

9.2: tetrahydrofuran; hexane / 0.33 h / -78 °C

10.1: NaH; CS₂; MeI / tetrahydrofuran

10.2: 70 percent / 2,2'-azobisisobutyronitrile; n-Bu₃SnH / toluene / 1.5 h / 80 °C

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

Reference yield:

: Thiocarbonic acid O-(((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-{(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}-methyl) ester O-methyl ester

: 247184-54-9
(2S,5R)-2-tert-Butyl-5-{(2S,6S,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-5-methyl-[1,3]dioxolan-4-one

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃;
DOI:10.1002/(SICI)1521-3773(19990802)38:15<2258::AID-ANIE2258>3.0.CO;2-#