((1S,5S,6R)-6-Formyl-5-methyl-cyclohex-2-enyl)-carbamic acid benzyl ester

Base Information

• Chemical Name: ((1S,5S,6R)-6-Formyl-5-methyl-cyclohex-2-enyl)-carbamic acid benzyl ester
• CAS No.: 87554-93-6
• Molecular Formula: C₁₆H₁₉NO₃
• Molecular Weight: 273.332

Synonyms:((1S,5S,6R)-6-Formyl-5-methyl-cyclohex-2-enyl)-carbamic acid benzyl ester

Chemical Property of ((1S,5S,6R)-6-Formyl-5-methyl-cyclohex-2-enyl)-carbamic acid benzyl ester

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Technology Process of ((1S,5S,6R)-6-Formyl-5-methyl-cyclohex-2-enyl)-carbamic acid benzyl ester

There total 3 articles about ((1S,5S,6R)-6-Formyl-5-methyl-cyclohex-2-enyl)-carbamic acid benzyl ester 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:

benzyl (buta-1,3-dien-1-yl)carbamate (71616-72-3) + crotonaldehyde (123-73-9,4170-30-3) → C16H19NO3 + ((1R,5R,6S)-6-Formyl-5-methyl-cyclohex-2-enyl)-carbamic acid benzyl ester (1029852-64-9) + ((1S,5S,6R)-6-Formyl-5-methyl-cyclohex-2-enyl)-carbamic acid benzyl ester (87554-93-6)

Guidance literature:

With C₅₃H₄₁F₅O₈P₂; In toluene; at -60 ℃; Overall yield = 34 %; enantioselective reaction;

DOI:10.1021/acscatal.5b02079

Reference yield:

1(E)-<(benzyloxycarbonyl)amino>-1,3-butadiene (65899-49-2) → ((1S,5S,6R)-6-Formyl-5-methyl-cyclohex-2-enyl)-carbamic acid benzyl ester (87554-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / BF₃*OEt₂ / toluene / 0.5 h / -78 °C

2: 1.) LiBH₄; 2.) NaIO₄ / 1.) THF; 2.) MeOH/H₂O, 12h

With sodium periodate; lithium borohydride; boron trifluoride diethyl etherate; In toluene;

DOI:10.1021/jo00171a072

Reference yield:

[(1S,5S,6R)-6-((R)-2-Hydroxy-3,3-dimethyl-butyryl)-5-methyl-cyclohex-2-enyl]-carbamic acid benzyl ester (87509-97-5) → ((1S,5S,6R)-6-Formyl-5-methyl-cyclohex-2-enyl)-carbamic acid benzyl ester (87554-93-6)

Guidance literature:

With sodium periodate; lithium borohydride; Yield given. Multistep reaction; 1.) THF; 2.) MeOH/H₂O, 12h;

DOI:10.1021/jo00171a072

upstream raw materials:

[(1S,5S,6R)-6-((R)-2-Hydroxy-3,3-dimethyl-butyryl)-5-methyl-cyclohex-2-enyl]-carbamic acid benzyl ester

1(E)-<(benzyloxycarbonyl)amino>-1,3-butadiene

benzyl (buta-1,3-dien-1-yl)carbamate

crotonaldehyde

Downstream raw materials:

[(1S,5S,6S)-5-Methyl-6-((E)-3-oxo-hex-1-enyl)-cyclohex-2-enyl]-carbamic acid benzyl ester

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