(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

Base Information

• Chemical Name: (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
• CAS No.: 126019-24-7
• Molecular Formula: C₁₉H₃₅IO₅Si
• Molecular Weight: 498.474

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 4 articles about (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 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: 79.0%

(1R*,2R*,3R*,4R*,5S*)-(3-methyl-3-oxetanyl)methyl 3-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4-iodo-5-methyl-cyclohexanecarboxylate (126019-23-6) → (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 (126019-24-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 6h;

DOI:10.1021/jo00295a032

Reference yield:

(1R*,2R*,3R*,4R*,5S*)-methyl 2,3-dihydroxy-4-iodo-5-methylcyclohexanecarboxylate (126019-21-4) → (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 (126019-24-7)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; titanium(IV) isopropylate; dmap; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00295a032

Reference yield:

(1R*,2R*,3R*,4R*,5S*)-methyl 3-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4-iodo-5-methylcyclohexanecarboxylate (126019-22-5) → (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 (126019-24-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / titanium tetraisopropoxide / 2.75 h / 80 °C

2: 79 percent / BF₃*Et₂O / CH₂Cl₂ / 6 h / 0 °C

With titanium(IV) isopropylate; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1021/jo00295a032

upstream raw materials:

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

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

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

(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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