(1S,2R,5R)-Methyl <2-(tert-Butyldimethylsilyloxy)methyl>-5-hydroxy-3-cyclohexene-1-carboxylate

Base Information

Chemical Name:(1S,2R,5R)-Methyl <2-(tert-Butyldimethylsilyloxy)methyl>-5-hydroxy-3-cyclohexene-1-carboxylate
CAS No.:130595-62-9
Molecular Formula:C₁₅H₂₈O₄Si
Molecular Weight:300.47
Hs Code.:

Synonyms:(1S,2R,5R)-Methyl <2-(tert-Butyldimethylsilyloxy)methyl>-5-hydroxy-3-cyclohexene-1-carboxylate

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Chemical Property of (1S,2R,5R)-Methyl <2-(tert-Butyldimethylsilyloxy)methyl>-5-hydroxy-3-cyclohexene-1-carboxylate

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Technology Process of (1S,2R,5R)-Methyl <2-(tert-Butyldimethylsilyloxy)methyl>-5-hydroxy-3-cyclohexene-1-carboxylate

There total 10 articles about (1S,2R,5R)-Methyl <2-(tert-Butyldimethylsilyloxy)methyl>-5-hydroxy-3-cyclohexene-1-carboxylate 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:

: 130695-72-6
(1S,2R,4R,5R)-2-Hydroxymethyl-4-iodo-6-oxabicyclo<3.2.1>octan-7-one

: 130595-62-9
(1S,2R,5R)-Methyl <2-(tert-Butyldimethylsilyloxy)methyl>-5-hydroxy-3-cyclohexene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 4.02 g / imidazole / dimethylformamide / 4 h / 0 °C

2: 95 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 4 h / Heating

3: 6.25 g / NaOMe / 1.5 h / 0 °C

With 1H-imidazole; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.38.1479

Reference yield:

: 104265-90-9
(1S,6R)-Methyl 6-Hydroxymethyl-3-cyclohexene-1-carboxylate

: 130595-62-9
(1S,2R,5R)-Methyl <2-(tert-Butyldimethylsilyloxy)methyl>-5-hydroxy-3-cyclohexene-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 15.70 g / imidazole / dimethylformamide / 10 h / 0 °C

2: 68 percent / 2 N NaOH / methanol / 10 h / Ambient temperature

3: 48 percent / NaHCO₃, I₂, KI / CH₂Cl₂; H₂O / 10 h / Ambient temperature

4: 95 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 4 h / Heating

5: 6.25 g / NaOMe / 1.5 h / 0 °C

With 1H-imidazole; sodium hydroxide; iodine; sodium methylate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.38.1479

Reference yield:

: 31139-02-3,31139-03-4,56124-48-2,88335-93-7,88335-94-8,93603-11-3
(1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid

: 130595-62-9
(1S,2R,5R)-Methyl <2-(tert-Butyldimethylsilyloxy)methyl>-5-hydroxy-3-cyclohexene-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 1) Et₃N, ethyl chloroformate, 2) NaBH₄ / 1) THF, -40 -> -20 deg C, 1 h, 2) H₂O, 0 deg C, 1 h

2: 15.70 g / imidazole / dimethylformamide / 10 h / 0 °C

3: 68 percent / 2 N NaOH / methanol / 10 h / Ambient temperature

4: 48 percent / NaHCO₃, I₂, KI / CH₂Cl₂; H₂O / 10 h / Ambient temperature

5: 95 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 4 h / Heating

6: 6.25 g / NaOMe / 1.5 h / 0 °C

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; iodine; sodium methylate; chloroformic acid ethyl ester; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; potassium iodide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.38.1479