tert-butyl (1S,6R)-3-formyl-6-hydroxycyclohex-3-enylcarbamate

Base Information

Chemical Name:tert-butyl (1S,6R)-3-formyl-6-hydroxycyclohex-3-enylcarbamate
CAS No.:1428733-28-1
Molecular Formula:C₁₂H₁₉NO₄
Molecular Weight:241.287
Hs Code.:

Synonyms:tert-butyl (1S,6R)-3-formyl-6-hydroxycyclohex-3-enylcarbamate

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Chemical Property of tert-butyl (1S,6R)-3-formyl-6-hydroxycyclohex-3-enylcarbamate

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Technology Process of tert-butyl (1S,6R)-3-formyl-6-hydroxycyclohex-3-enylcarbamate

There total 10 articles about tert-butyl (1S,6R)-3-formyl-6-hydroxycyclohex-3-enylcarbamate 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: 70.0%

: 1428733-27-0
tert-butyl (3aS,7aR)-5-formyl-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d]oxazole-3(2H)-carboxylate

: 1428733-28-1
tert-butyl (1S,6R)-3-formyl-6-hydroxycyclohex-3-enylcarbamate

Guidance literature:: With lithium chloride; In water; acetic acid; at 20 ℃; for 1h;
DOI:10.1055/s-0032-1317948

Reference yield:

: 53100-44-0,160347-90-0
L-N-t-butoxycarbonylpyroglutamic acid

: 1428733-28-1
tert-butyl (1S,6R)-3-formyl-6-hydroxycyclohex-3-enylcarbamate

Guidance literature:: Multi-step reaction with 9 steps

1.1: isobutyl chloroformate; triethylamine / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 1.25 h / 0 - 20 °C / Inert atmosphere

2.1: triethylsilane; palladium 10% on activated carbon / acetone / 0.75 h / 20 °C / Inert atmosphere

3.1: indium / tetrahydrofuran; water / 16 h

4.1: sodium tetrahydroborate / tetrahydrofuran; water / 18 h / 20 °C

5.1: toluene-4-sulfonic acid / dichloromethane / 0.75 h / 20 °C

6.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

7.1: triethylamine / dichloromethane / 18 h / 20 °C

8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / 35 °C / Inert atmosphere

9.1: lithium chloride / water; acetic acid / 1 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triethylsilane; indium; sodium tetrahydroborate; palladium 10% on activated carbon; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; lithium chloride; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; water; acetic acid; acetone;
DOI:10.1055/s-0032-1317948

Reference yield:

: 185303-87-1
tert-butyl (S)-2-formyl-5-oxopyrrolidine-1-carboxylate

: 1428733-28-1
tert-butyl (1S,6R)-3-formyl-6-hydroxycyclohex-3-enylcarbamate

Guidance literature:: Multi-step reaction with 7 steps

1: indium / tetrahydrofuran; water / 16 h

2: sodium tetrahydroborate / tetrahydrofuran; water / 18 h / 20 °C

3: toluene-4-sulfonic acid / dichloromethane / 0.75 h / 20 °C

4: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

5: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; water / 3 h / 20 °C

6: N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide / dichloromethane / 16 h / 35 °C

7: lithium chloride / water; acetic acid / 1 h / 20 °C

With indium; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride; Dess-Martin periodane; toluene-4-sulfonic acid; lithium chloride; potassium hydroxide; In tetrahydrofuran; dichloromethane; water; acetic acid;
DOI:10.1055/s-0032-1317948