(R)-6-{5,5-Dimethyl-2-[(R)-4-(toluene-4-sulfonylmethyl)-hexyl]-[1,3]dioxan-2-yl}-2-methyl-hexan-1-ol

Base Information

• Chemical Name: (R)-6-{5,5-Dimethyl-2-[(R)-4-(toluene-4-sulfonylmethyl)-hexyl]-[1,3]dioxan-2-yl}-2-methyl-hexan-1-ol
• CAS No.: 128057-09-0
• Molecular Formula: C₂₇H₄₆O₅S
• Molecular Weight: 482.725
• Mol file: 128057-09-0.mol

Synonyms:(R)-6-{5,5-Dimethyl-2-[(R)-4-(toluene-4-sulfonylmethyl)-hexyl]-[1,3]dioxan-2-yl}-2-methyl-hexan-1-ol

Chemical Property of (R)-6-{5,5-Dimethyl-2-[(R)-4-(toluene-4-sulfonylmethyl)-hexyl]-[1,3]dioxan-2-yl}-2-methyl-hexan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-{5,5-Dimethyl-2-[(R)-4-(toluene-4-sulfonylmethyl)-hexyl]-[1,3]dioxan-2-yl}-2-methyl-hexan-1-ol

There total 13 articles about (R)-6-{5,5-Dimethyl-2-[(R)-4-(toluene-4-sulfonylmethyl)-hexyl]-[1,3]dioxan-2-yl}-2-methyl-hexan-1-ol 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: 86.0%

(2R,11R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(toluene-4-sulfonylmethyl)-tridecan-7-one (128057-23-8) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → (R)-6-{5,5-Dimethyl-2-[(R)-4-(toluene-4-sulfonylmethyl)-hexyl]-[1,3]dioxan-2-yl}-2-methyl-hexan-1-ol (128057-09-0)

Guidance literature:

toluene-4-sulfonic acid; In benzene; at 80 ℃;

DOI:10.1021/jo00298a016

Reference yield:

methyl 6-hydroxycaproate (4547-43-7) → (R)-6-{5,5-Dimethyl-2-[(R)-4-(toluene-4-sulfonylmethyl)-hexyl]-[1,3]dioxan-2-yl}-2-methyl-hexan-1-ol (128057-09-0)

Guidance literature:

Multi-step reaction with 11 steps

1: i-Pr₂NEt / CH₂Cl₂ / Ambient temperature

2: LiOH, aq. MeOH / tetrahydrofuran

3: 1) NEt₃ / 1) THF, 0 deg C

4: 1) NaN(TMS)2 / 1) THF, 2) -78 to -30 deg C

5: 84 percent / LiAlH₄ / diethyl ether / 0 °C

6: 1) I₂, Ph₃P, imidazole / 1) CH₂Cl₂, 0 deg C to RT, 2) DMF, RT

7: 97 percent / H₂, conc. HCl / Pt black / methanol / 760 Torr

8: 85 percent / (COCl)2, DMSO, NEt₃ / -78 deg C to RT

9: 83 percent / diethyl ether / 0 °C

10: 97 percent / PCC on Al₂O₃ / CH₂Cl₂

11: 86 percent / TsOH / benzene / 80 °C

With 1H-imidazole; hydrogenchloride; methanol; lithium hydroxide; pyridinium chlorochromate absorbed on neutral alumina; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; iodine; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; toluene-4-sulfonic acid; platinum; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo00298a016

Reference yield:

6-Benzyloxymethoxy-hexanoic acid → (R)-6-{5,5-Dimethyl-2-[(R)-4-(toluene-4-sulfonylmethyl)-hexyl]-[1,3]dioxan-2-yl}-2-methyl-hexan-1-ol (128057-09-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) NEt₃ / 1) THF, 0 deg C

2: 1) NaN(TMS)2 / 1) THF, 2) -78 to -30 deg C

3: 84 percent / LiAlH₄ / diethyl ether / 0 °C

4: 1) I₂, Ph₃P, imidazole / 1) CH₂Cl₂, 0 deg C to RT, 2) DMF, RT

5: 97 percent / H₂, conc. HCl / Pt black / methanol / 760 Torr

6: 85 percent / (COCl)2, DMSO, NEt₃ / -78 deg C to RT

7: 83 percent / diethyl ether / 0 °C

8: 97 percent / PCC on Al₂O₃ / CH₂Cl₂

9: 86 percent / TsOH / benzene / 80 °C

With 1H-imidazole; hydrogenchloride; pyridinium chlorochromate absorbed on neutral alumina; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; iodine; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; triphenylphosphine; toluene-4-sulfonic acid; platinum; In methanol; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo00298a016

upstream raw materials:

(2R,11R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(toluene-4-sulfonylmethyl)-tridecan-7-one

2,2-Dimethyl-1,3-propanediol

methyl 6-hydroxycaproate

6-(((benzyloxy)methylene)oxy)-2-ethylhexanoic acid