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

Base Information

• Chemical Name: (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol
• CAS No.: 105938-03-2
• Molecular Formula: C₂₈H₃₂O₅
• Molecular Weight: 448.559
• Mol file: 105938-03-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-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: 82.0%

methyllithium (917-54-4) + 3,4,6-tri-O-benzyl-D-glucal epoxide (74372-90-0) → (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol (105938-03-2)

Guidance literature:

methyllithium; With copper(l) iodide; In tetrahydrofuran; hexane; at 0 ℃;

3,4,6-tri-O-benzyl-D-glucal epoxide; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 1h;

DOI:10.1016/S0040-4020(02)00057-1

Reference yield: 77.0%

dimethyl sulfate (77-78-1) + triphenyl(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)stannane (161145-52-4) → (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol (105938-03-2)

Guidance literature:

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

DOI:10.1002/hlca.19940770730

Reference yield: 50.0%

C27H28LiO5(1-)*Li(1+) + methyl iodide (74-88-4) → 3,4,6-tri-O-benzyl-α-D-glucopyranose (40246-26-2) + (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol (105938-03-2)

Guidance literature:

With thien-2-yl(cyano)copper lithium; In tetrahydrofuran; hexane; at -78 ℃; Product distribution; further methylating agents, further electrophiles, stereoselectivity;

DOI:10.1002/hlca.19940770730

upstream raw materials:

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol

dimethyl sulfate

triphenyl(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)stannane

methyl iodide

Downstream raw materials:

Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yl ester