Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

• Chemical Name: Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS No.: 124814-02-4
• Molecular Formula: C₅₁H₅₄N₂O₁₃S
• Molecular Weight: 935.061

Synonyms:

Chemical Property of Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

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Technology Process of Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 8 articles about Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 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 2,3,6-tri-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-α-D-mannopyranoside (124814-01-3) + N,N`-sulfuryldiimidazole (7189-69-7) → Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (124814-02-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -30 ℃;

DOI:10.1016/0008-6215(89)84070-4

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (124814-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-p-sulfonic acid / acetonitrile / 1 h / Ambient temperature

2: NaH (60percent dispersion in oil) / dimethylformamide / -30 °C

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0008-6215(89)84070-4

Reference yield:

benzyl-O-β-D-glucopyranoside (97590-76-6) → Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-6-((2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (124814-02-4)

Guidance literature:

Multi-step reaction with 5 steps

1: NaOAc / 4 h / 110 °C

2: 87 percent / 1.) crushed molecular sieves (4 Angstroem); 2.) trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1.) r.t., 0.5 h; 2.) -20 deg C to r.t.

3: 1percent NaOMe / methanol / Ambient temperature

4: toluene-p-sulfonic acid / acetonitrile / 1 h / Ambient temperature

5: NaH (60percent dispersion in oil) / dimethylformamide / -30 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium acetate; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0008-6215(89)84070-4

upstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-α-D-mannopyranoside

N,N`-sulfuryldiimidazole

benzaldehyde dimethyl acetal

benzyl-O-β-D-glucopyranoside

Downstream raw materials:

methyl 4-O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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