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

Base Information

• Chemical Name: (1R^*,2R^*,3R^*,4R^*,5S^*)-methyl 3-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4-iodo-5-methylcyclohexanecarboxylate
• CAS No.: 126019-22-5
• Molecular Formula: C₁₅H₂₉IO₄Si
• Molecular Weight: 428.383
• Mol file: 126019-22-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1R^*,2R^*,3R^*,4R^*,5S^*)-methyl 3-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-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: 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: 80.0%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + (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-methyl-3-oxetanyl)methyl 3-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-4-iodo-5-methyl-cyclohexanecarboxylate (126019-23-6)

Guidance literature:

With titanium(IV) isopropylate; at 80 ℃; for 2.75h;

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^*)-methyl 2,3-dihydroxy-4-iodo-5-methylcyclohexanecarboxylate

tert-butyldimethylsilyl chloride

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

(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