(2S)-1-(benzyloxy)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-4-yn-2-ol

Base Information

• Chemical Name: (2S)-1-(benzyloxy)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-4-yn-2-ol
• CAS No.: 853929-20-1
• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.44
• Mol file: 853929-20-1.mol

Synonyms:(2S)-1-(benzyloxy)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-4-yn-2-ol

Chemical Property of (2S)-1-(benzyloxy)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-4-yn-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-1-(benzyloxy)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-4-yn-2-ol

There total 2 articles about (2S)-1-(benzyloxy)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-4-yn-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: 85.0%

1-(tetrahydropyranyloxy)-4-pentyn (62992-46-5) + (S)-benzyl glycidyl ether (2930-05-4,14618-80-5,89616-40-0,16495-13-9) → (2S)-1-(benzyloxy)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-4-yn-2-ol (853929-20-1)

Guidance literature:

1-(tetrahydropyranyloxy)-4-pentyn; With n-butyllithium; In tetrahydrofuran; at -70 - 20 ℃;

(S)-benzyl glycidyl ether; With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.tetlet.2005.03.175

Reference yield:

Benzyloxymethyl-oxiran (2930-05-4) → (2S)-1-(benzyloxy)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-4-yn-2-ol (853929-20-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 45 percent / H₂O / (R,R)-(salen)Co(III)(OAc) / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran / -70 - 20 °C

2.2: 85 percent / BF₃*Et₂O / tetrahydrofuran / -78 °C

With n-butyllithium; water; (R,R)-(salen)Co(III)(OAc); In tetrahydrofuran;

DOI:10.1016/j.tetlet.2005.03.175

Reference yield: 92.0%

(2S)-1-(benzyloxy)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-4-yn-2-ol (853929-20-1) + benzoyl chloride (98-88-4) → Benzoic acid (S)-1-benzyloxymethyl-7-(tetrahydro-pyran-2-yloxy)-hept-3-ynyl ester (853929-27-8)

Guidance literature:

With pyridine; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2005.03.175

upstream raw materials:

1-(tetrahydropyranyloxy)-4-pentyn

(S)-benzyl glycidyl ether

Benzyloxymethyl-oxiran

Downstream raw materials:

Benzoic acid (S)-1-benzyloxymethyl-7-(tetrahydro-pyran-2-yloxy)-hept-3-ynyl ester

Benzoic acid (Z)-(S)-1-formyl-6-methoxycarbonyl-hex-3-enyl ester

Benzoic acid (Z)-(S)-1-hydroxymethyl-6-methoxycarbonyl-hex-3-enyl ester

Benzoic acid (Z)-(S)-1-((E)-2-iodo-vinyl)-6-methoxycarbonyl-hex-3-enyl ester