(R)-1-(2-Allyl-[1,3]dithian-2-yl)-4-benzyloxy-3,3-dimethyl-butan-2-ol

Base Information

• Chemical Name: (R)-1-(2-Allyl-[1,3]dithian-2-yl)-4-benzyloxy-3,3-dimethyl-butan-2-ol
• CAS No.: 202406-55-1
• Molecular Formula: C₂₀H₃₀O₂S₂
• Molecular Weight: 366.589
• Mol file: 202406-55-1.mol

Synonyms:(R)-1-(2-Allyl-[1,3]dithian-2-yl)-4-benzyloxy-3,3-dimethyl-butan-2-ol

Chemical Property of (R)-1-(2-Allyl-[1,3]dithian-2-yl)-4-benzyloxy-3,3-dimethyl-butan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-(2-Allyl-[1,3]dithian-2-yl)-4-benzyloxy-3,3-dimethyl-butan-2-ol

There total 1 articles about (R)-1-(2-Allyl-[1,3]dithian-2-yl)-4-benzyloxy-3,3-dimethyl-butan-2-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: 92.0%

2-allyl-1,3-dithiane (63382-29-6) + (S)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane (111080-21-8) → (R)-1-(2-Allyl-[1,3]dithian-2-yl)-4-benzyloxy-3,3-dimethyl-butan-2-ol (202406-55-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -30 ℃;

DOI:10.1016/j.tet.2006.05.077

Reference yield: 77.0%

(R)-1-(2-Allyl-[1,3]dithian-2-yl)-4-benzyloxy-3,3-dimethyl-butan-2-ol (202406-55-1) → (R)-8-Benzyloxy-6-hydroxy-7,7-dimethyl-oct-1-en-4-one (909016-28-0)

Guidance literature:

(R)-1-(2-Allyl-[1,3]dithian-2-yl)-4-benzyloxy-3,3-dimethyl-butan-2-ol; With bis-[(trifluoroacetoxy)iodo]benzene; In methanol; at 0 ℃; for 0.75h;

With acetic acid; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.1016/j.tet.2006.05.077

Reference yield:

(R)-1-(2-Allyl-[1,3]dithian-2-yl)-4-benzyloxy-3,3-dimethyl-butan-2-ol (202406-55-1) → 2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-(2-hydroxy-1,1-dimethyl-ethyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester (909016-32-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: (CF₃CO₂)2IPh / methanol / 0.75 h / 0 °C

1.2: 77 percent / aq. AcOH / tetrahydrofuran / 0.25 h / 20 °C

2.1: 86 percent / Me₄NBH(OAc)3; AcOH / acetonitrile / -40 - -30 °C

3.1: 97 percent / (+/-)-camphorsulfonic acid / acetone / 19 h / 20 °C

4.1: OsO₄; N-methylmorpholine-N-oxide; H₂O / 2-methyl-propan-2-ol; acetone / 2 h / 20 °C

5.1: 1.53 g / aq. NaIO₄; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; acetone / 0.5 h / 20 °C

6.1: 88 percent / Et₂Zn; RhCl(PPh₃)3 / tetrahydrofuran; hexane / 0.58 h / 0 °C

7.1: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

8.1: PPTS / methanol / 1 h / 20 °C

9.1: 100 percent / imidazole / dimethylformamide / 2 h / 0 °C

10.1: 96 percent / H₂ / Pd(OH)2/C / dioxane / 2 h / 20 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; RhCl(PPh₃)3; camphor-10-sulfonic acid; water; hydrogen; diethylzinc; pyridinium p-toluenesulfonate; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; tetramethylammonium triacetoxyborohydride; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; 7.1: Swern oxidation;

DOI:10.1016/j.tet.2006.05.077

upstream raw materials:

2-allyl-1,3-dithiane

(S)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane

Downstream raw materials:

(R)-8-Benzyloxy-6-hydroxy-7,7-dimethyl-oct-1-en-4-one

2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-10-trimethylsilanyl-deca-3,7-dien-9-ynyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester

2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2,6-dihydroxy-1,1,4-trimethyl-9-trityloxy-nona-3,7-dienyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid

2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-9-trityloxy-nona-3,7-dienyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester