(2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-ol
• CAS No.: 160318-52-5
• Molecular Formula: C₂₈H₃₁IO₅
• Molecular Weight: 574.456
• Mol file: 160318-52-5.mol

Synonyms:(2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-ol

Chemical Property of (2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-ol

There total 3 articles about (2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-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: 99.0%

(((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxytetrahydro-2H-pyran-2-yl)methyl)mercury(II) chloride (93125-49-6) → (2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-ol (160318-52-5)

Guidance literature:

With iodine;

Reference yield:

(2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol (93125-77-0) → (2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-ol (160318-52-5)

Guidance literature:

With mercury(II) diacetate; iodine; Yield given. Multistep reaction; 1.) THF, RT, 72 h, 2.) THF, RT, 15 h;

DOI:10.1016/0008-6215(94)00191-X

Reference yield:

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) → (2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-ol (160318-52-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: zinc dibromide / tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C / Inert atmosphere

2.1: mercury(II) diacetate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

2.2: 0.5 h

3.1: iodine / dichloromethane / 16 h / Inert atmosphere

With mercury(II) diacetate; iodine; zinc dibromide; In tetrahydrofuran; dichloromethane;

upstream raw materials:

(2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol

(((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxytetrahydro-2H-pyran-2-yl)methyl)mercury(II) chloride

2,3,5-tri-O-benzyl-D-arabinofuranose

Downstream raw materials:

2,6-anhydro-4,5,7-tri-O-benzyl-1-deoxy-D-gluco-1-heptenitol

diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

(((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-yl)oxy)(tert-butyl)dimethylsilane

diethyl (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methyl)phosphonate