(3R,4R,5S)-3-(2-Bromo-allyloxy)-4,5-dihydroxy-5-methyl-cyclohex-1-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (3R,4R,5S)-3-(2-Bromo-allyloxy)-4,5-dihydroxy-5-methyl-cyclohex-1-enecarboxylic acid methyl ester
• CAS No.: 109346-57-8
• Molecular Formula: C₁₂H₁₇BrO₅
• Molecular Weight: 321.168
• Mol file: 109346-57-8.mol

Synonyms:(3R,4R,5S)-3-(2-Bromo-allyloxy)-4,5-dihydroxy-5-methyl-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property of (3R,4R,5S)-3-(2-Bromo-allyloxy)-4,5-dihydroxy-5-methyl-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S)-3-(2-Bromo-allyloxy)-4,5-dihydroxy-5-methyl-cyclohex-1-enecarboxylic acid methyl ester

There total 6 articles about (3R,4R,5S)-3-(2-Bromo-allyloxy)-4,5-dihydroxy-5-methyl-cyclohex-1-enecarboxylic acid methyl 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: 69.0%

(3R,4R,5S)-3,4,5-Trihydroxy-5-methyl-cyclohex-1-enecarboxylic acid methyl ester (109346-56-7,110269-96-0) + 2-bromoallyl bromide (513-31-5) → (3R,4R,5S)-3-(2-Bromo-allyloxy)-4,5-dihydroxy-5-methyl-cyclohex-1-enecarboxylic acid methyl ester (109346-57-8)

Guidance literature:

With thallium (I) ethoxide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)85135-7

Reference yield:

(+/-)-4c-Acetoxy-2c,3c-dihydroxy-5-oxo-cyclohexan-1r-carbonsaeure (10226-76-3) → (3R,4R,5S)-3-(2-Bromo-allyloxy)-4,5-dihydroxy-5-methyl-cyclohex-1-enecarboxylic acid methyl ester (109346-57-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 63 percent

2: 93 percent / CSA

3: 72 percent / tetrahydrofuran / 0.08 h / 0 °C

4: NaOMe

5: 69 percent / TlOEt / dimethylformamide

With camphor-10-sulfonic acid; sodium methylate; thallium (I) ethoxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)85135-7

Reference yield:

(+/-)-exo-cis-3-Acetoxy-4t,5t-dihydroxy-3,6-epoxy-(1rH)-cyclohexan-1,2-dicarbonsaeure (10226-75-2,92243-68-0) → (3R,4R,5S)-3-(2-Bromo-allyloxy)-4,5-dihydroxy-5-methyl-cyclohex-1-enecarboxylic acid methyl ester (109346-57-8)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂O

2: 63 percent

3: 93 percent / CSA

4: 72 percent / tetrahydrofuran / 0.08 h / 0 °C

5: NaOMe

6: 69 percent / TlOEt / dimethylformamide

With camphor-10-sulfonic acid; water; sodium methylate; thallium (I) ethoxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)85135-7

upstream raw materials:

(3R,4R,5S)-3,4,5-Trihydroxy-5-methyl-cyclohex-1-enecarboxylic acid methyl ester

2-bromoallyl bromide

(+/-)-4c-Acetoxy-2c,3c-dihydroxy-5-oxo-cyclohexan-1r-carbonsaeure

(+/-)-exo-cis-3-Acetoxy-4t,5t-dihydroxy-3,6-epoxy-(1rH)-cyclohexan-1,2-dicarbonsaeure

Downstream raw materials:

(3S,4S,5R)-4,5-Diacetoxy-3-(2-bromo-allyloxy)-5-methyl-cyclohex-1-enecarboxylic acid methyl ester