(2S,3S,5S,6R)-3,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-one O-benzyl-oxime

Base Information

• Chemical Name: (2S,3S,5S,6R)-3,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-one O-benzyl-oxime
• CAS No.: 844863-28-1
• Molecular Formula: C₄₇H₄₅NO₆
• Molecular Weight: 719.877

Synonyms:(2S,3S,5S,6R)-3,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-one O-benzyl-oxime

Chemical Property of (2S,3S,5S,6R)-3,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-one O-benzyl-oxime

Chemical Property:

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Technology Process of (2S,3S,5S,6R)-3,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-one O-benzyl-oxime

There total 2 articles about (2S,3S,5S,6R)-3,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-one O-benzyl-oxime 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: 72.0%

N-benzyloxyamine (622-33-3) + (2S,3R,5R,6R)-3,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-one (844863-25-8) → (2S,3S,5S,6R)-3,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-one O-benzyl-oxime (844863-28-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In toluene; at 80 ℃;

DOI:10.1055/s-2004-835651

Reference yield:

methyl 2,4-di-O-benzyl-6-O-trityl-α-D-mannopyranoside (79218-73-8) → (2S,3S,5S,6R)-3,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-one O-benzyl-oxime (844863-28-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / PCC / 20 °C

2: 72 percent / PPTS / toluene / 80 °C

With pyridinium p-toluenesulfonate; pyridinium chlorochromate; In toluene;

DOI:10.1055/s-2004-835651

Reference yield: 82.0%

(2S,3S,5S,6R)-3,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-one O-benzyl-oxime (844863-28-1) → (2R,3S,5S,6S)-3,5-Bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-4-one O-benzyl-oxime (844863-30-5)

Guidance literature:

With iron(III) chloride; In dichloromethane; at 20 ℃;

DOI:10.1055/s-2004-835651

upstream raw materials:

N-benzyloxyamine

(2S,3R,5R,6R)-3,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-one

methyl 2,4-di-O-benzyl-6-O-trityl-α-D-mannopyranoside

Downstream raw materials:

(2R,3S,5S,6S)-3,5-Bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-4-one O-benzyl-oxime

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