((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-butyl-tetrahydro-pyran-2-yl)-methanol

Base Information

• Chemical Name: ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-butyl-tetrahydro-pyran-2-yl)-methanol
• CAS No.: 891783-17-8
• Molecular Formula: C₃₁H₃₈O₅
• Molecular Weight: 490.64
• Mol file: 891783-17-8.mol

Synonyms:((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-butyl-tetrahydro-pyran-2-yl)-methanol

Chemical Property of ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-butyl-tetrahydro-pyran-2-yl)-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-butyl-tetrahydro-pyran-2-yl)-methanol

There total 2 articles about ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-butyl-tetrahydro-pyran-2-yl)-methanol 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%

(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-butyltetrahydro-2H-pyran (141100-75-6,141196-24-9) → ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-butyl-tetrahydro-pyran-2-yl)-methanol (891783-17-8)

Guidance literature:

(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-butyltetrahydro-2H-pyran; With acetic anhydride; trifluoroacetic acid; at 20 ℃; for 2h;

With sodium methylate; In methanol; at 20 ℃; for 0.166667h;

DOI:10.3390/10080843

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-butyl-tetrahydro-pyran-2-yl)-methanol (891783-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diethyl ether / 0.5 h / -78 °C

1.2: 88 percent / Et₃SiH; BF₃₈OEt₂ / CH₂Cl₂ / 0.5 h / -78 °C

2.1: TFA; Ac₂O / 2 h / 20 °C

2.2: 85 percent / MeONa / methanol / 0.17 h / 20 °C

With acetic anhydride; trifluoroacetic acid; In diethyl ether;

DOI:10.3390/10080843

Reference yield: 94.0%

((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-butyl-tetrahydro-pyran-2-yl)-methanol (891783-17-8) → (2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-butyl-6-iodomethyl-tetrahydro-pyran (891783-18-9)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 70 ℃; for 0.5h;

DOI:10.3390/10080843

upstream raw materials:

(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-butyltetrahydro-2H-pyran

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Downstream raw materials:

(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-butyl-6-iodomethyl-tetrahydro-pyran

(2S,3S,4R,5S)-3,4,5-Tris-benzyloxy-2-butyl-6-methylene-tetrahydro-pyran