Diazo-acetic acid (3R,4R)-4-hydroxy-3-methyl-bicyclohexyl-1,1',3'-trien-3-ylmethyl ester

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Chemical Name:Diazo-acetic acid (3R,4R)-4-hydroxy-3-methyl-bicyclohexyl-1,1',3'-trien-3-ylmethyl ester
CAS No.:137819-40-0
Molecular Formula:C₁₆H₂₀N₂O₃
Molecular Weight:288.346
Hs Code.:

Synonyms:Diazo-acetic acid (3R,4R)-4-hydroxy-3-methyl-bicyclohexyl-1,1',3'-trien-3-ylmethyl ester

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Chemical Property of Diazo-acetic acid (3R,4R)-4-hydroxy-3-methyl-bicyclohexyl-1,1',3'-trien-3-ylmethyl ester

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Technology Process of Diazo-acetic acid (3R,4R)-4-hydroxy-3-methyl-bicyclohexyl-1,1',3'-trien-3-ylmethyl ester

There total 8 articles about Diazo-acetic acid (3R,4R)-4-hydroxy-3-methyl-bicyclohexyl-1,1',3'-trien-3-ylmethyl 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:

: 137819-34-2
7-(tert-Butyl-dimethyl-silanyloxymethyl)-1,4-dioxa-spiro[4.5]dec-6-en-8-one

: 137819-40-0
Diazo-acetic acid (3R,4R)-4-hydroxy-3-methyl-bicyclohexyl-1,1',3'-trien-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: BH₃ / CBS-(S)-catalyst / tetrahydrofuran / 0.5 h / 37 °C

2: 93 percent / HOAc / H₂O / 3 h / 23 °C

3: 88 percent / CuSO₄ / 4 h / 60 °C

4: 2) HMPA / 1) Et₂O, -20 to 0 deg C, 1h, 2) THF, 0 deg C, 2h

6: 92 percent / 1M HCl / tetrahydrofuran / 0.5 h / 23 °C

7: 1) PhNMe₂, 2) Et₃N / 1) CH₂Cl₂, -25 deg C, 30 min, 2) 0 to 23 deg C, 30 min

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; borane; copper(II) sulfate; acetic acid; N,N-dimethyl-aniline; triethylamine; CBS-(S)-catalyst; In tetrahydrofuran; water;
DOI:10.1016/S0040-4039(00)93418-X

Reference yield:

: 63028-11-5
cyclohexa-1,3-dien-1-yl trifluoromethanesulfonate

: 137819-40-0
Diazo-acetic acid (3R,4R)-4-hydroxy-3-methyl-bicyclohexyl-1,1',3'-trien-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

2: 92 percent / 1M HCl / tetrahydrofuran / 0.5 h / 23 °C

3: 1) PhNMe₂, 2) Et₃N / 1) CH₂Cl₂, -25 deg C, 30 min, 2) 0 to 23 deg C, 30 min

With hydrogenchloride; N,N-dimethyl-aniline; triethylamine; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)93418-X

Reference yield:

: (R)-4-Hydroxy-3-hydroxymethyl-cyclohex-2-enone

: 137819-40-0
Diazo-acetic acid (3R,4R)-4-hydroxy-3-methyl-bicyclohexyl-1,1',3'-trien-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / CuSO₄ / 4 h / 60 °C

2: 2) HMPA / 1) Et₂O, -20 to 0 deg C, 1h, 2) THF, 0 deg C, 2h

4: 92 percent / 1M HCl / tetrahydrofuran / 0.5 h / 23 °C

5: 1) PhNMe₂, 2) Et₃N / 1) CH₂Cl₂, -25 deg C, 30 min, 2) 0 to 23 deg C, 30 min

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(II) sulfate; N,N-dimethyl-aniline; triethylamine; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)93418-X