(S)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)ethane-1,2-diol

Base Information

Chemical Name:(S)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)ethane-1,2-diol
CAS No.:1449375-02-3
Molecular Formula:C₂₄H₃₆O₉
Molecular Weight:468.544
Hs Code.:

(S)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)ethane-1,2-diol

Synonyms:(S)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)ethane-1,2-diol

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Chemical Property of (S)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)ethane-1,2-diol

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Technology Process of (S)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)ethane-1,2-diol

There total 17 articles about (S)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)ethane-1,2-diol 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:

: 1449375-01-2
(3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran

: 1449375-02-3
(S)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)ethane-1,2-diol

: 1449375-03-4
(R)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)ethane-1,2-diol

Guidance literature:: With potassium osmate(VI) dihydrate; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 5 ℃; for 24h; pH=7; Overall yield = 100 %; Overall yield = 220 mg; diastereoselective reaction;
DOI:10.1016/j.tet.2013.05.067

Reference yield:

: C₂₆H₃₄O₅Si

: 1449375-02-3
(S)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)ethane-1,2-diol

Guidance literature:: Multi-step reaction with 9 steps

1.1: dichloromethane / 1 h / 20 °C

2.1: diisobutylaluminium hydride / toluene; hexane / -78 - 0 °C

3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 0 - 20 °C

4.1: AD-mix-β; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium osmate(VI) dihydrate; methanesulfonamide / tert-butyl alcohol / pH 7

5.1: toluene-4-sulfonic acid / acetone / 4 h / 0 - 20 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C

7.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.33 h / -60 °C

7.2: -60 - 20 °C

8.1: potassium tert-butylate / tetrahydrofuran / -10 - 20 °C

8.2: -10 - 20 °C

9.1: hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); potassium carbonate; potassium osmate(VI) dihydrate; methanesulfonamide / tert-butyl alcohol / pH 7

With potassium osmate(VI) dihydrate; oxalyl dichloride; methanesulfonamide; AD-mix-β; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; hydroquinidein 1,4-phthalazinediyl diether; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tetrahydrofuran; hexane; dichloromethane; acetone; toluene; tert-butyl alcohol; 4.1: |Sharpless Dihydroxylation / 7.1: |Swern Oxidation / 7.2: |Swern Oxidation / 9.1: |Sharpless Dihydroxylation;
DOI:10.1016/j.tet.2013.05.067

Reference yield:

: 1449375-00-1
C₂₃H₃₂O₈

: 1449375-02-3
(S)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)ethane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium tert-butylate / tetrahydrofuran / -10 - 20 °C

1.2: -10 - 20 °C

2.1: hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); potassium carbonate; potassium osmate(VI) dihydrate; methanesulfonamide / tert-butyl alcohol / pH 7

With potassium osmate(VI) dihydrate; methanesulfonamide; potassium tert-butylate; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); In tetrahydrofuran; tert-butyl alcohol; 2.1: |Sharpless Dihydroxylation;
DOI:10.1016/j.tet.2013.05.067