methyl 2,2¹-anhydro-4,6-O-benzylidene-3-C-hydroxyacetyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,2¹-anhydro-4,6-O-benzylidene-3-C-hydroxyacetyl-α-D-glucopyranoside
CAS No.:110889-42-4
Molecular Formula:C₁₆H₁₈O₇
Molecular Weight:322.315
Hs Code.:

methyl 2,2<sup>1</sup>-anhydro-4,6-O-benzylidene-3-C-hydroxyacetyl-α-D-glucopyranoside

Synonyms:methyl 2,2¹-anhydro-4,6-O-benzylidene-3-C-hydroxyacetyl-α-D-glucopyranoside

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Chemical Property of methyl 2,2¹-anhydro-4,6-O-benzylidene-3-C-hydroxyacetyl-α-D-glucopyranoside

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Technology Process of methyl 2,2¹-anhydro-4,6-O-benzylidene-3-C-hydroxyacetyl-α-D-glucopyranoside

There total 7 articles about methyl 2,2¹-anhydro-4,6-O-benzylidene-3-C-hydroxyacetyl-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: 78.0%

: 110889-40-2,110889-43-5
methyl 2,2¹-anhydro-4,6-O-benzylidene-3-C-<(R)-1,2-dihydroxyethyl>-α-D-glucopyranoside

: 110889-42-4
methyl 2,2¹-anhydro-4,6-O-benzylidene-3-C-hydroxyacetyl-α-D-glucopyranoside

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1 h, room temperature;
DOI:10.1016/S0008-6215(00)90006-5

Reference yield:

: 28642-65-1
methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose

: 110889-42-4
methyl 2,2¹-anhydro-4,6-O-benzylidene-3-C-hydroxyacetyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 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

5: sodium methoxide / methanol

6: 72 percent / camphorsulfonyl chloride, pyridine / 20 h / Ambient temperature

7: 78 percent / dimethyl sulfoxide, oxalyl chloride, triethylamine / CH₂Cl₂ / 1 h, room temperature

With pyridine; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; water; sodium methylate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; camphorsulfonyl chloride; triethylamine; N-cyclohexyl-cyclohexanamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; tert-butyl alcohol;
DOI:10.1016/S0008-6215(00)90006-5

Reference yield:

: 110889-24-2
(4aR,6S,7R,8aS)-8-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 110889-42-4
methyl 2,2¹-anhydro-4,6-O-benzylidene-3-C-hydroxyacetyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine

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

3: sodium methoxide / methanol

4: 72 percent / camphorsulfonyl chloride, pyridine / 20 h / Ambient temperature

5: 78 percent / dimethyl sulfoxide, oxalyl chloride, triethylamine / CH₂Cl₂ / 1 h, room temperature

With pyridine; osmium(VIII) oxide; oxalyl dichloride; water; sodium methylate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; camphorsulfonyl chloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1016/S0008-6215(00)90006-5