(1S)-1-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-(4-methoxybenzyloxy)-3-pentyn-1-ol

Base Information

• Chemical Name: (1S)-1-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-(4-methoxybenzyloxy)-3-pentyn-1-ol
• CAS No.: 532932-75-5
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386
• Mol file: 532932-75-5.mol

Synonyms:(1S)-1-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-(4-methoxybenzyloxy)-3-pentyn-1-ol

Chemical Property of (1S)-1-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-(4-methoxybenzyloxy)-3-pentyn-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-1-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-(4-methoxybenzyloxy)-3-pentyn-1-ol

There total 1 articles about (1S)-1-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-(4-methoxybenzyloxy)-3-pentyn-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: 51.0%

(2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol (93367-10-3,212375-57-0) + 3-(4-methoxybenzyloxy)propyne (4039-83-2) → (1S)-1-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-(4-methoxybenzyloxy)-3-pentyn-1-ol (532932-75-5)

Guidance literature:

With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 6h;

DOI:10.1016/S0957-4166(03)00038-7

Reference yield: 80.0%

benzenesulfonyl chloride (98-09-9) + (1S)-1-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-(4-methoxybenzyloxy)-3-pentyn-1-ol (532932-75-5) → (4S)-4-[(1'S)-5'-(4-methoxybenzyloxy)-1'-phenylsulfonyloxy-3'-pentynyl]-2,2-dimethyl-1,3-dioxolane (532932-76-6)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1016/S0957-4166(03)00038-7

Reference yield:

(1S)-1-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-5-(4-methoxybenzyloxy)-3-pentyn-1-ol (532932-75-5) → (4S)-4-[(1'S,3'Z)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane (532932-78-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / Et₃N / CH₂Cl₂ / 6 h / 20 °C

2: 71 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

3: 94 percent / quinoline; H₂ / Lindlar's catalyst / ethyl acetate / 6 h / 20 °C

With quinoline; hydrogen; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In dichloromethane; water; ethyl acetate;

DOI:10.1016/S0957-4166(03)00038-7

upstream raw materials:

(2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol

3-(4-methoxybenzyloxy)propyne

Downstream raw materials:

(4S)-4-[(1'S)-5'-(4-methoxybenzyloxy)-1'-phenylsulfonyloxy-3'-pentynyl]-2,2-dimethyl-1,3-dioxolane

(4S)-4-[(1'S,3'Z)-4'-formyl-1'-phenylsulfonyloxy-3'-butenyl]-2,2-dimethyl-1,3-dioxolane

(2S,3R,4S,6R)-6-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4-methoxy-2-phenyltetrahydro-2H-pyran-3-ol

(4S)-4-[(1'S,3'Z)-5'-hydroxy-1'-phenylsulfonyloxy-3'-pentenyl]-2,2-dimethyl-1,3-dioxolane