(1R^*,2R^*,3R^*,4R^*,5S^*)-methyl 2,3-dihydroxy-4-iodo-5-methylcyclohexanecarboxylate

Base Information

• Chemical Name: (1R^*,2R^*,3R^*,4R^*,5S^*)-methyl 2,3-dihydroxy-4-iodo-5-methylcyclohexanecarboxylate
• CAS No.: 126019-21-4
• Molecular Formula: C₉H₁₅IO₄
• Molecular Weight: 314.12

Synonyms:(1R^*,2R^*,3R^*,4R^*,5S^*)-methyl 2,3-dihydroxy-4-iodo-5-methylcyclohexanecarboxylate

Chemical Property of (1R^*,2R^*,3R^*,4R^*,5S^*)-methyl 2,3-dihydroxy-4-iodo-5-methylcyclohexanecarboxylate

Chemical Property:

Purity/Quality:

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Technology Process of (1R^*,2R^*,3R^*,4R^*,5S^*)-methyl 2,3-dihydroxy-4-iodo-5-methylcyclohexanecarboxylate

There total 1 articles about (1R^*,2R^*,3R^*,4R^*,5S^*)-methyl 2,3-dihydroxy-4-iodo-5-methylcyclohexanecarboxylate 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:

methanol (67-56-1) + (1R*,2S*,5S*)-2-acetoxy-5-methyl-3-cyclohexene-1-carboxylic acid (126019-11-2) → (1R*,2R*,3R*,4S*,5S*)-methyl 2,4-dihydroxy-3-iodo-5-methylcyclohexanecarboxylate (126019-20-3) + (1R*,2R*,3R*,4R*,5S*)-methyl 2,3-dihydroxy-4-iodo-5-methylcyclohexanecarboxylate (126019-21-4)

Guidance literature:

With N-iodo-succinimide; sodium hydrogencarbonate; acetyl chloride; Yield given. Multistep reaction. Yields of byproduct given; 1. THF, 18 h, reflux 2. 3 h, reflux;

DOI:10.1021/jo00295a032

Reference yield: 97.0%

(1R*,2R*,3R*,4R*,5S*)-methyl 2,3-dihydroxy-4-iodo-5-methylcyclohexanecarboxylate (126019-21-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (1R*,2R*,3R*,4R*,5S*)-methyl 3-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4-iodo-5-methylcyclohexanecarboxylate (126019-22-5)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; for 21h; Ambient temperature;

DOI:10.1021/jo00295a032

Reference yield:

(1R*,2R*,3R*,4R*,5S*)-methyl 2,3-dihydroxy-4-iodo-5-methylcyclohexanecarboxylate (126019-21-4) → (1S,2S,3R,5S,6S)-2-[(E)-3-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxymethyl-propenyl]-5-methyl-3-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-7-oxa-bicyclo[4.1.0]heptan-2-ol

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / 4-(dimethylamino)pyridine, imidazole / dimethylformamide / 21 h / Ambient temperature

2: 80 percent / titanium tetraisopropoxide / 2.75 h / 80 °C

3: 79 percent / BF₃*Et₂O / CH₂Cl₂ / 6 h / 0 °C

4: 88 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 4 h

5: 1. trifluoroacetic anhydride, DMSO 2. NEt₃ / 1. 30 min, -78 deg C 2. warming up over 10 min to 0 deg C

6: 1. n-BuLi / 1. THF, hexane, 1.5 h, -35 deg C 2. 30 min, -78 deg C then -45 deg C, 1.5 h

With 1H-imidazole; titanium(IV) isopropylate; dmap; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00295a032

upstream raw materials:

methanol

(1R^*,2S^*,5S^*)-2-acetoxy-5-methyl-3-cyclohexene-1-carboxylic acid

Downstream raw materials:

(1R^*,2R^*,3R^*,4R^*,5S^*)-methyl 3-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4-iodo-5-methylcyclohexanecarboxylate

(1R^*,2R^*,3R^*,4R^*,5S^*)-3-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4-iodo-5-methyl-1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)cyclohexane

(1R^*,2R^*,3R^*,4R^*,5S^*)-(3-methyl-3-oxetanyl)methyl 3-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4-iodo-5-methyl-cyclohexanecarboxylate

(1S^*,2R^*,4S^*,5S^*,6R^*)-9(E)-<2-<(tert-butyldiphenylsilyl)oxy>-1-ethylidene>-1,5-dihydroxy-4-methyl-2-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-7-oxabicyclo<4.3.0>nonane

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