Technology Process of (1R,4S)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-3-one
There total 25 articles about (1R,4S)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-3-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:
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![{(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-2-[(1R,4R)-1-methoxy-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentyl]-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yloxy}-tert-butyl-dimethyl-silane](/Databaselist/images/loading.webp)
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218785-31-0
{(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-2-[(1R,4R)-1-methoxy-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentyl]-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yloxy}-tert-butyl-dimethyl-silane
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218785-33-2
(1R,4S)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-3-one
- Guidance literature:
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{(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-2-[(1R,4R)-1-methoxy-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentyl]-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yloxy}-tert-butyl-dimethyl-silane;
With
osmium(VIII) oxide; N-methyl-2-indolinone;
With
sodium periodate;
DOI:10.1021/ja992134m
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91751-27-8,91797-99-8,91798-00-4,91798-01-5,106357-24-8,106357-26-0,106357-27-1,106357-25-9
(3R,4R,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene
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218785-33-2
(1R,4S)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-3-one
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: TBAF / tetrahydrofuran
2.1: PPTS
3.1: 86 percent / O2; aq. Cu(OAc)2; PdCl2 / N,N-dimethyl-acetamide / 30 h
4.1: 97 percent / KHMDS
5.1: (Bu3Sn)2; n-BuLi; lithium 2-thienylcyanocuprate
5.2: NBS
6.1: t-BuLi / diethyl ether / 0.5 h / -78 - 0 °C
6.2: lithium 2-thienylcyanocuprate / 0.5 h / -78 - -45 °C
6.3: 83 percent / 48 h / -5 °C
7.1: 96 percent / KHMDS
8.1: OsO4; NMO
8.2: 87 percent / NaIO4
With
osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; copper diacetate; tetrabutyl ammonium fluoride; tert.-butyl lithium; oxygen; bis(tri-n-butyltin); pyridinium p-toluenesulfonate; potassium hexamethylsilazane; thien-2-yl(cyano)copper lithium; palladium dichloride;
In
tetrahydrofuran; diethyl ether; N,N-dimethyl acetamide;
1.1: desilylation / 2.1: acetalization / 3.1: Oxidation / 4.1: enol protection / 5.1: Substitution / 5.2: Substitution / 6.1: Metallation / 6.2: Addition / 6.3: coupling / 7.1: Methylation / 8.1: Oxidation / 8.2: cleavage;
DOI:10.1021/ja992134m
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218785-33-2
(1R,4S)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-3-one
- Guidance literature:
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Multi-step reaction with 15 steps
1.1: DMSO; (COCl)2; Et3N / CH2Cl2 / -78 °C
2.1: BF3*Et2O / CH2Cl2 / 0 °C
3.1: 85 percent / TsOH / dimethylformamide
4.1: n-BuLi; HMPA / tetrahydrofuran
4.2: 81 percent / DMPU / tetrahydrofuran / -20 °C
5.1: 95 percent / 2,6-lutidine
6.1: 94 percent / DIBAL / CH2Cl2 / -78 - 0 °C
7.1: 87 percent / SO3*pyridine; DMSO; Et3N / CH2Cl2
8.1: tetrahydrofuran / -78 °C
9.1: 95 percent / TBAF / 60 °C
10.1: 76 percent / HgCl2; CaCO3 / tetrahydrofuran
11.1: 30 percent aq. H2O2; PhCN; KHCO3 / methanol / 0 °C
12.1: 98 percent / Et3N
13.1: t-BuLi / diethyl ether / 0.5 h / -78 - 0 °C
13.2: lithium 2-thienylcyanocuprate / 0.5 h / -78 - -45 °C
13.3: 83 percent / 48 h / -5 °C
14.1: 96 percent / KHMDS
15.1: OsO4; NMO
15.2: 87 percent / NaIO4
With
2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; pyridine-SO3 complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; benzonitrile; triethylamine; calcium carbonate; mercury dichloride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
1.1: Oxidation / 2.1: thioacetalization; deacetalization / 3.1: acetalization / 4.1: Metallation / 4.2: Addition / 5.1: silylation / 6.1: reductive cleavage / 7.1: Oxidation / 8.1: Grignard reaction / 9.1: desilylation / 10.1: Cyclization / 11.1: Epoxidation / 12.1: silylation / 13.1: Metallation / 13.2: Addition / 13.3: coupling / 14.1: Methylation / 15.1: Oxidation / 15.2: cleavage;
DOI:10.1021/ja992134m
