(2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-carbaldehyde

Base Information

• Chemical Name: (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-carbaldehyde
• CAS No.: 103931-55-1
• Molecular Formula: C₆₁H₆₂O₁₁
• Molecular Weight: 971.157

Synonyms:

Chemical Property of (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-carbaldehyde

There total 4 articles about (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-carbaldehyde 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:

1,3,4-tri-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (103931-54-0) → (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-carbaldehyde (103931-55-1)

Guidance literature:

With phosphoric acid; dicyclohexyl-carbodiimide; In pyridine; dimethyl sulfoxide; for 6h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90395-1

Reference yield:

benzyl chloride (100-44-7) → (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-carbaldehyde (103931-55-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / sodium hydride / dimethylsulfoxide / 2 h / Ambient temperature

2: 78 percent / 80percent trifluoroacetic acid / CHCl₃; H₂O / 0.33 h / Ambient temperature

3: orthophosphoric acid, DCC / dimethylsulfoxide; pyridine / 6 h / Ambient temperature

With phosphoric acid; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In pyridine; chloroform; water; dimethyl sulfoxide;

DOI:10.1016/S0008-6215(00)90395-1

Reference yield:

2,3,6,1',3',4'-hexa-O-acetyl-6'-O-trityl-sucrose (40010-26-2) → (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-carbaldehyde (103931-55-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / sodium hydride / dimethylsulfoxide / 2 h / Ambient temperature

2: 78 percent / 80percent trifluoroacetic acid / CHCl₃; H₂O / 0.33 h / Ambient temperature

3: orthophosphoric acid, DCC / dimethylsulfoxide; pyridine / 6 h / Ambient temperature

With phosphoric acid; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In pyridine; chloroform; water; dimethyl sulfoxide;

DOI:10.1016/S0008-6215(00)90395-1

upstream raw materials:

1,3,4-tri-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

benzyl chloride

2,3,6,1',3',4'-hexa-O-acetyl-6'-O-trityl-sucrose

1,3,4-tri-O-benzyl-6-O-trityl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

1,3,4-tri-O-benzyl-7-deoxy-(β-D-altro,α-L-galacto)-hept-2-ulofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

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