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

Base Information

Chemical Name:tert-butyl (1R,2S,3R,4S,6R)-2,3,4-trihydroxy-6-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexylcarbamate
CAS No.:1402069-85-5
Molecular Formula:C₁₉H₂₇NO₈
Molecular Weight:397.425
Hs Code.:

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

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Chemical Property of tert-butyl (1R,2S,3R,4S,6R)-2,3,4-trihydroxy-6-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexylcarbamate

Chemical Property:

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Technology Process of tert-butyl (1R,2S,3R,4S,6R)-2,3,4-trihydroxy-6-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexylcarbamate

There total 9 articles about tert-butyl (1R,2S,3R,4S,6R)-2,3,4-trihydroxy-6-(7-methoxybenzo[d][1,3]dioxol-5-yl)cyclohexylcarbamate 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:

: C₁₉H₂₅NO₈

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

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1002/chem.201201649

Reference yield:

: 1402069-91-3
C₁₉H₂₅NO₇

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

Guidance literature:: Multi-step reaction with 8 steps

1: methanol; diethyl ether / 1 h

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

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

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

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

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

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

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

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

Reference yield:

: 654061-13-9
(R)-4-(7-methoxybenzo[1,3]dioxol-5-yl)but-3-en-2-ol

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

Guidance literature:: Multi-step reaction with 10 steps

1.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 20 °C

2.1: tert-butyldimethylsilyl chloride; lithium hexamethyldisilazane / tetrahydrofuran / 20 h / -78 - 20 °C

2.2: 0 - 20 °C

3.1: methanol; diethyl ether / 1 h

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

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

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

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

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

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

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

With dmap; perchloric acid; palladium 10% on activated carbon; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; palladium diacetate; L-Selectride; sodium hydrogencarbonate; tert-butyldimethylsilyl chloride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; sodium bis(2-methoxyethoxy)aluminium dihydride; p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile; 4.1: Wacker oxidation;
DOI:10.1002/chem.201201649