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

Base Information

• Chemical Name: methyl 2,2¹-di-O-acetyl-4,6-O-benzylidene-3-C-<(R)-1,2-dihydroxyethyl>-α-D-glucopyranoside
• CAS No.: 110889-38-8
• Molecular Formula: C₂₀H₂₆O₁₀
• Molecular Weight: 426.42

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

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

Chemical Property:

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

There total 4 articles about methyl 2,2¹-di-O-acetyl-4,6-O-benzylidene-3-C-<(R)-1,2-dihydroxyethyl>-α-D-glucopyranoside 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: 57.0%

methyl 2,21-di-O-acetyl-4,6-O-benzylidene-3-C-<(z)-2-hydroxyethylidene>-α-D-ribo-hexopyranoside (110889-25-3) → methyl 2,21-di-O-acetyl-4,6-O-benzylidene-3-C-<(R)-1,2-dihydroxyethyl>-α-D-glucopyranoside (110889-38-8)

Guidance literature:

With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In tetrahydrofuran; tert-butyl alcohol; Ambient temperature;

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

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-<(R)-1,2-dihydroxyethyl>-α-D-glucopyranoside (110889-38-8)

Guidance literature:

Multi-step reaction with 4 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

4: 57 percent / 4-methylmorpholine N-oxide, osmium tetraoxide, water / 2-methyl-propan-2-ol; tetrahydrofuran / Ambient temperature

With pyridine; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; water; 4-methylmorpholine N-oxide; N-cyclohexyl-cyclohexanamine; In tetrahydrofuran; diethyl ether; tert-butyl alcohol;

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

Reference yield:

(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-<(R)-1,2-dihydroxyethyl>-α-D-glucopyranoside (110889-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: 57 percent / 4-methylmorpholine N-oxide, osmium tetraoxide, water / 2-methyl-propan-2-ol; tetrahydrofuran / Ambient temperature

With pyridine; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In tetrahydrofuran; tert-butyl alcohol;

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

upstream raw materials:

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

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

(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-3-C-(ethoxycarbonylmethylene)-α-D-ribo-hexopyranoside

Downstream raw materials:

(4aR,6S,7R,8R,8aR)-8-((R)-1,2-Dihydroxy-ethyl)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

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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