(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-2-(4-hydroxy-benzyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-2-(4-hydroxy-benzyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol
• CAS No.: 464177-72-8
• Molecular Formula: C₂₈H₃₂O₇
• Molecular Weight: 480.558

Synonyms:(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-2-(4-hydroxy-benzyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol

Chemical Property of (2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-2-(4-hydroxy-benzyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-2-(4-hydroxy-benzyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol

There total 3 articles about (2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-2-(4-hydroxy-benzyloxymethyl)-6-methoxy-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: 63.0%

(2R,3S,4S,5R,6R)-2-(4-Allyloxy-benzyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ol (464177-71-7) → (2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-2-(4-hydroxy-benzyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol (464177-72-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol;

DOI:10.1016/S0040-4039(02)00851-1

Reference yield:

4-allyloxybenzyl chloride (32078-38-9) → (2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-2-(4-hydroxy-benzyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol (464177-72-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Bu₂Sn(OMe)2; Bu₄NI / toluene

2: 63 percent / Pd(PPh₃)4 / ethanol

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide; dibutyldimethoxytin; In ethanol; toluene;

DOI:10.1016/S0040-4039(02)00851-1

Reference yield:

methyl 2,3-di-O-benzyl-β-D-galactopyranoside (6988-40-5,17791-36-5,29388-46-3,31873-34-4,33164-03-3,51842-19-4,52526-60-0,61117-12-2,87392-25-4,117605-35-3) → (2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-2-(4-hydroxy-benzyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol (464177-72-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Bu₂Sn(OMe)2; Bu₄NI / toluene

2: 63 percent / Pd(PPh₃)4 / ethanol

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide; dibutyldimethoxytin; In ethanol; toluene;

DOI:10.1016/S0040-4039(02)00851-1

upstream raw materials:

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

4-allyloxybenzyl chloride

methyl 2,3-di-O-benzyl-β-D-galactopyranoside

Downstream raw materials:

6-[4-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-phenoxy]-hexanoic acid

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