(+)-<1(R)-methyl-2(R)-hydroxy-5(R)-(1(R)-((tosyloxy)methyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal

Base Information

• Chemical Name: (+)-<1(R)-methyl-2(R)-hydroxy-5(R)-(1(R)-((tosyloxy)methyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal
• CAS No.: 105764-29-2
• Molecular Formula: C₂₅H₄₀O₆S
• Molecular Weight: 468.655
• Mol file: 105764-29-2.mol

Synonyms:(+)-<1(R)-methyl-2(R)-hydroxy-5(R)-(1(R)-((tosyloxy)methyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal

Chemical Property of (+)-<1(R)-methyl-2(R)-hydroxy-5(R)-(1(R)-((tosyloxy)methyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-<1(R)-methyl-2(R)-hydroxy-5(R)-(1(R)-((tosyloxy)methyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal

There total 14 articles about (+)-<1(R)-methyl-2(R)-hydroxy-5(R)-(1(R)-((tosyloxy)methyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal 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: 62.0%

(1R,2R,3R)-2-[1,3]Dioxolan-2-ylmethyl-3-((R)-1-hydroxymethyl-5-methyl-hexyl)-2-methyl-cyclopentanol (105764-28-1) + p-toluenesulfonyl chloride (98-59-9) → (+)-<1(R)-methyl-2(R)-hydroxy-5(R)-(1(R)-((tosyloxy)methyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal (105764-29-2)

Guidance literature:

With dmap; In dichloromethane; for 8h; Ambient temperature;

DOI:10.1021/jo00376a049

Reference yield:

(R)-7a-methyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione (17553-86-5,19576-08-0,20007-98-1,17553-89-8) → (+)-<1(R)-methyl-2(R)-hydroxy-5(R)-(1(R)-((tosyloxy)methyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal (105764-29-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) triethanolamine, 60 deg C, 20 min, 2.) triethanolamine, 60 deg C, 24 h

2: 88 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / Ambient temperature

3: 71 percent / HCl, H₂ / 5percent Pd/C / acetic acid; methanol / 4 h / Ambient temperature

4: 98 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 0.5 h / Ambient temperature

5: 1.) CuI, BF₃*Et₂O / 1.) THF, a) -30 deg C, 30 min, b) RT, 5 min, 2.) THF, RT, 10 min

6: 26 percent / p-toluenesulfonic acid / 4 h / Heating

7: 1.) O₃, 2.) LiOH / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) THF, RT, 1 h

8: 70 percent / camphossulfonic acid (CSA) / benzene / 1.5 h / Heating

9: 1.06 g / LiAlH₄ / tetrahydrofuran / 6 h / Ambient temperature

10: 62 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 8 h / Ambient temperature

With hydrogenchloride; dmap; lithium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; benzene;

DOI:10.1021/jo00376a049

Reference yield:

(-)-(7aR)-4-<(phenylthio)methyl>-5,6,7,7a-tetrahydro-7a-methylindan-1,5-dione (105764-24-7) → (+)-<1(R)-methyl-2(R)-hydroxy-5(R)-(1(R)-((tosyloxy)methyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal (105764-29-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 88 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / Ambient temperature

2: 71 percent / HCl, H₂ / 5percent Pd/C / acetic acid; methanol / 4 h / Ambient temperature

3: 98 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 0.5 h / Ambient temperature

4: 1.) CuI, BF₃*Et₂O / 1.) THF, a) -30 deg C, 30 min, b) RT, 5 min, 2.) THF, RT, 10 min

5: 26 percent / p-toluenesulfonic acid / 4 h / Heating

6: 1.) O₃, 2.) LiOH / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) THF, RT, 1 h

7: 70 percent / camphossulfonic acid (CSA) / benzene / 1.5 h / Heating

8: 1.06 g / LiAlH₄ / tetrahydrofuran / 6 h / Ambient temperature

9: 62 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 8 h / Ambient temperature

With hydrogenchloride; dmap; lithium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; benzene;

DOI:10.1021/jo00376a049

upstream raw materials:

hypochlorous acid 4-methylbenzene sulfonic anhydride

(1R,2R,3R)-2-[1,3]Dioxolan-2-ylmethyl-3-((R)-1-hydroxymethyl-5-methyl-hexyl)-2-methyl-cyclopentanol

p-toluenesulfonyl chloride

(R)-7a-methyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione

Downstream raw materials:

(+)-<1(R)-methyl-2(R)-((methoxymethyl)oxy)-5(R)-(1(R)-((tosyloxy)methyl)-5-methylhexyl)cyclopentyl>acetaldehyde ethylene acetal