methyl 2,2¹-di-O-acetyl-4,6-O-benzylidene-3-C-<(z)-2-hydroxyethylidene>-α-D-ribo-hexopyranoside

Base Information

• Chemical Name: methyl 2,2¹-di-O-acetyl-4,6-O-benzylidene-3-C-<(z)-2-hydroxyethylidene>-α-D-ribo-hexopyranoside
• CAS No.: 110889-25-3
• Molecular Formula: C₂₀H₂₄O₈
• Molecular Weight: 392.406

Synonyms:methyl 2,2¹-di-O-acetyl-4,6-O-benzylidene-3-C-<(z)-2-hydroxyethylidene>-α-D-ribo-hexopyranoside

Chemical Property of methyl 2,2¹-di-O-acetyl-4,6-O-benzylidene-3-C-<(z)-2-hydroxyethylidene>-α-D-ribo-hexopyranoside

Chemical Property:

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Technology Process of methyl 2,2¹-di-O-acetyl-4,6-O-benzylidene-3-C-<(z)-2-hydroxyethylidene>-α-D-ribo-hexopyranoside

There total 3 articles about methyl 2,2¹-di-O-acetyl-4,6-O-benzylidene-3-C-<(z)-2-hydroxyethylidene>-α-D-ribo-hexopyranoside 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:

methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose (28642-65-1) → methyl 2,21-di-O-acetyl-4,6-O-benzylidene-3-C-<(z)-2-hydroxyethylidene>-α-D-ribo-hexopyranoside (110889-25-3)

Guidance literature:

Multi-step reaction with 3 steps

1: dicyclohexylamine, butyllithium / tetrahydrofuran / 1.) -78 deg C, 1 h 2.) -25 deg C, 1 h then 0 deg C, 1 h

2: lithium aluminium hydride / diethyl ether / 0.5 h / Ambient temperature

3: pyridine

With pyridine; lithium aluminium tetrahydride; n-butyllithium; N-cyclohexyl-cyclohexanamine; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0008-6215(00)90006-5

Reference yield:

methyl 2-O-benzoyl-4,6-O-benzylidene-3-C-(ethoxycarbonylmethylene)-α-D-ribo-hexopyranoside (110889-23-1,110889-47-9) → methyl 2,21-di-O-acetyl-4,6-O-benzylidene-3-C-<(z)-2-hydroxyethylidene>-α-D-ribo-hexopyranoside (110889-25-3)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium hydride / diethyl ether / 0.5 h / Ambient temperature

2: pyridine

With pyridine; lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1016/S0008-6215(00)90006-5

Reference yield:

acetic anhydride (108-24-7) + (4aR,6S,7R,8aS)-8-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (110889-24-2) → methyl 2,21-di-O-acetyl-4,6-O-benzylidene-3-C-<(z)-2-hydroxyethylidene>-α-D-ribo-hexopyranoside (110889-25-3)

Guidance literature:

With pyridine; Yield given;

DOI:10.1016/S0008-6215(00)90006-5

upstream raw materials:

acetic anhydride

(4aR,6S,7R,8aS)-8-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose

methyl 2-O-benzoyl-4,6-O-benzylidene-3-C-(ethoxycarbonylmethylene)-α-D-ribo-hexopyranoside

Downstream raw materials:

methyl 2,2¹-di-O-acetyl-4,6-O-benzylidene-3-C-<(R)-1,2-dihydroxyethyl>-α-D-glucopyranoside

methyl 2,2¹-anhydro-4,6-O-benzylidene-3-C-<(S)-1,2-dihydroxyethyl>-α-D-glucopyranoside

methyl 2,2¹-anhydro-4,6-O-benzylidene-3-C-<(R)-1,2-dihydroxyethyl>-α-D-glucopyranoside

Acetic acid (3S,3aS,4R,5R,7S,7aR)-3,3a,4-tris-benzyloxy-7-methoxy-hexahydro-furo[2,3-c]pyran-5-ylmethyl ester

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