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

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-6-Allyloxy-2-allyloxymethyl-4,5-bis-benzyloxy-tetrahydro-pyran-3-ol
• CAS No.: 97818-00-3
• Molecular Formula: C₂₆H₃₂O₆
• Molecular Weight: 440.536
• Mol file: 97818-00-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (2R,3S,4S,5R,6R)-6-Allyloxy-2-allyloxymethyl-4,5-bis-benzyloxy-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: 58.7%

allyl 2,3-di-Ο-benzyl-β-D-galactopyranoside (97817-99-7) + allyl bromide (106-95-6) → allyl-4-O-allyl-2,3-di-O-benzyl-β-D-galactopyranoside (97818-01-4) + (2R,3S,4S,5R,6R)-6-Allyloxy-2-allyloxymethyl-4,5-bis-benzyloxy-tetrahydro-pyran-3-ol (97818-00-3)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; for 18h; Heating;

Reference yield:

allyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside (71925-96-7) → (2R,3S,4S,5R,6R)-6-Allyloxy-2-allyloxymethyl-4,5-bis-benzyloxy-tetrahydro-pyran-3-ol (97818-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90.9 percent / aq. sulfuric acid / ethanol / 10 h / Heating

2: 58.7 percent / aq. NaOH, Bu₄NHSO₄ / CH₂Cl₂ / 18 h / Heating

With sodium hydroxide; sulfuric acid; tetra(n-butyl)ammonium hydrogensulfate; In ethanol; dichloromethane;

Reference yield: 98.7%

(2R,3S,4S,5R,6R)-6-Allyloxy-2-allyloxymethyl-4,5-bis-benzyloxy-tetrahydro-pyran-3-ol (97818-00-3) + methyl iodide (74-88-4) → allyl-6-O-allyl-2,3-di-O-benzyl-4-O-methyl-β-D-galactopyranoside (97818-02-5)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; for 1h; Ambient temperature;

upstream raw materials:

allyl 2,3-di-Ο-benzyl-β-D-galactopyranoside

allyl bromide

allyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

Downstream raw materials:

allyl-6-O-allyl-2,3-di-O-benzyl-4-O-methyl-β-D-galactopyranoside

3,4-di-O-benzyl-2-O-methyl-L-lyxopyranose

2,3-di-O-benzyl-4-O-methyl-D-galactitol

2,3-di-O-benzyl-4-O-methyl-α/β-D-galactopyranose