(2R,3S)-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2-methylheptan-1-one

Base Information

Chemical Name:(2R,3S)-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2-methylheptan-1-one
CAS No.:1027311-89-2
Molecular Formula:C₂₆H₃₉NO₆S
Molecular Weight:493.665
Hs Code.:

Synonyms:(2R,3S)-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2-methylheptan-1-one

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Chemical Property of (2R,3S)-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2-methylheptan-1-one

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Technology Process of (2R,3S)-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2-methylheptan-1-one

There total 4 articles about (2R,3S)-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2-methylheptan-1-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: 83.0%

: 125664-95-1
N-propionyl-(2R)-bornane-(10,2)-sultam

: 131375-69-4
5-((4-methoxybenzyl)oxy)pentanal

: 1027311-89-2
(2R,3S)-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2-methylheptan-1-one

Guidance literature:: N-propionyl-(2R)-bornane-(10,2)-sultam; With triethyl borane; trifluorormethanesulfonic acid; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; at -5 ℃; for 0.333333h;

5-((4-methoxybenzyl)oxy)pentanal; In hexane; dichloromethane; at -78 ℃; for 3h; optical yield given as %de;
DOI:10.1002/chem.201101799

Reference yield:

: 131375-63-8
5-(4-methoxybenzyloxy)-1-pentanol

: 1027311-89-2
(2R,3S)-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2-methylheptan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C

1.2: -78 - 20 °C

2.1: triethyl borane; trifluorormethanesulfonic acid; N-ethyl-N,N-diisopropylamine / hexane; dichloromethane / 0.33 h / -5 °C

2.2: 3 h / -78 °C

With oxalyl dichloride; triethyl borane; trifluorormethanesulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.2: Aldol condensation;
DOI:10.1002/chem.201101799

Reference yield:

: 111-29-5
1 ,5-pentanediol

: 1027311-89-2
(2R,3S)-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2-methylheptan-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 4.5 h / 0 °C / Reflux

1.2: 17 h / Reflux

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C

2.2: -78 - 20 °C

3.1: triethyl borane; trifluorormethanesulfonic acid; N-ethyl-N,N-diisopropylamine / hexane; dichloromethane / 0.33 h / -5 °C

3.2: 3 h / -78 °C

With oxalyl dichloride; triethyl borane; trifluorormethanesulfonic acid; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; mineral oil; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.2: Aldol condensation;
DOI:10.1002/chem.201101799