(1S,2R,3S,4R,5R)-4-(tert-butoxycarbonylamino)-5-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexane-1,2,3-triyl triacetate

Base Information

Chemical Name:(1S,2R,3S,4R,5R)-4-(tert-butoxycarbonylamino)-5-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexane-1,2,3-triyl triacetate
CAS No.:1402069-86-6
Molecular Formula:C₂₅H₃₃NO₁₁
Molecular Weight:523.537
Hs Code.:

Synonyms:(1S,2R,3S,4R,5R)-4-(tert-butoxycarbonylamino)-5-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexane-1,2,3-triyl triacetate

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Chemical Property of (1S,2R,3S,4R,5R)-4-(tert-butoxycarbonylamino)-5-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexane-1,2,3-triyl triacetate

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Technology Process of (1S,2R,3S,4R,5R)-4-(tert-butoxycarbonylamino)-5-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexane-1,2,3-triyl triacetate

There total 9 articles about (1S,2R,3S,4R,5R)-4-(tert-butoxycarbonylamino)-5-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexane-1,2,3-triyl triacetate 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: 92.0%

: 1402069-85-5
tert-butyl (1R,2S,3R,4S,6R)-2,3,4-trihydroxy-6-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexylcarbamate

: 108-24-7
acetic anhydride

: 1402069-86-6
(1S,2R,3S,4R,5R)-4-(tert-butoxycarbonylamino)-5-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexane-1,2,3-triyl triacetate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h;
DOI:10.1002/chem.201201649

Reference yield:

: C₁₉H₂₅NO₈

: 1402069-86-6
(1S,2R,3S,4R,5R)-4-(tert-butoxycarbonylamino)-5-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexane-1,2,3-triyl triacetate

Guidance literature:: Multi-step reaction with 2 steps

1: L-Selectride / tetrahydrofuran / 0.5 h / -78 °C

2: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

With dmap; L-Selectride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.201201649

Reference yield:

: 1402069-79-7
(2R,3R,E)-Methyl 2-(tert-butoxycarbonylamino)-3-(7-methoxybenzo[d]-ACHTUNGTRENUNG[1,3]dioxol-5-yl)hex-4-enoate

: 1402069-86-6
(1S,2R,3S,4R,5R)-4-(tert-butoxycarbonylamino)-5-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexane-1,2,3-triyl triacetate

Guidance literature:: Multi-step reaction with 8 steps

1: perchloric acid; palladium diacetate; p-benzoquinone / water; acetonitrile / 6 h / 20 °C

2: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C

3: camphor-10-sulfonic acid / toluene / 4 h / 80 °C

4: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.5 h / 0 °C

5: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / 2 h / 0 - 20 °C

6: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 20 °C

7: L-Selectride / tetrahydrofuran / 0.5 h / -78 °C

8: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

With dmap; perchloric acid; palladium 10% on activated carbon; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; palladium diacetate; L-Selectride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; 1: Wacker oxidation;
DOI:10.1002/chem.201201649