(3aS,5R,6S,6aR)-6-Benzyloxy-5-dimethoxymethyl-tetrahydro-furo[3,2-b]furan-2-one

Base Information

• Chemical Name: (3aS,5R,6S,6aR)-6-Benzyloxy-5-dimethoxymethyl-tetrahydro-furo[3,2-b]furan-2-one
• CAS No.: 139534-92-2
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.331

Synonyms:(3aS,5R,6S,6aR)-6-Benzyloxy-5-dimethoxymethyl-tetrahydro-furo[3,2-b]furan-2-one

Chemical Property of (3aS,5R,6S,6aR)-6-Benzyloxy-5-dimethoxymethyl-tetrahydro-furo[3,2-b]furan-2-one

Chemical Property:

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Technology Process of (3aS,5R,6S,6aR)-6-Benzyloxy-5-dimethoxymethyl-tetrahydro-furo[3,2-b]furan-2-one

There total 5 articles about (3aS,5R,6S,6aR)-6-Benzyloxy-5-dimethoxymethyl-tetrahydro-furo[3,2-b]furan-2-one 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: 79.0%

methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-enofuranuronate (108266-98-4) → (3aS,5R,6S,6aR)-6-Benzyloxy-5-dimethoxymethyl-tetrahydro-furo[3,2-b]furan-2-one (139534-92-2)

Guidance literature:

methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-enofuranuronate; With methanol; sulfuric acid; for 2h; Reflux;

With sodium hydrogencarbonate; In methanol; at 35 ℃; for 1h;

DOI:10.1016/j.bmcl.2008.08.097

Reference yield: 74.0%

methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-cyclohexylidene-α-D-xylo-hept-5-enofuranuronate (645403-03-8) → C16H20O6 + (3aS,5R,6S,6aR)-6-Benzyloxy-5-dimethoxymethyl-tetrahydro-furo[3,2-b]furan-2-one (139534-92-2)

Guidance literature:

methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-cyclohexylidene-α-D-xylo-hept-5-enofuranuronate; With sulfuric acid; In methanol; for 4.5h; Reflux;

With sodium hydrogencarbonate; In methanol; at 35 ℃; for 1h;

DOI:10.1016/j.bmcl.2008.08.093

Reference yield: 65.0%

ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-48-3) → (3aS,5R,6S,6aR)-6-Benzyloxy-5-dimethoxymethyl-tetrahydro-furo[3,2-b]furan-2-one (139534-92-2)

Guidance literature:

sulfuric acid; In methanol; for 2h; Heating;

DOI:10.1016/0040-4039(91)80139-W

upstream raw materials:

ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-cyclohexylidene-α-D-xylo-hept-5-enofuranuronate

methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-enofuranuronate

Downstream raw materials:

C₁₄H₁₄O₅

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