Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-((2R,3R,4S,5R,6S)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-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-2-phenyl-6-((2R,3R,4S,5R,6S)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
CAS No.:124813-95-2
Molecular Formula:C₅₇H₅₈N₂O₁₃S
Molecular Weight:1011.16
Hs Code.:

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

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Chemical Property of Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-((2R,3R,4S,5R,6S)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-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-2-phenyl-6-((2R,3R,4S,5R,6S)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-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-2-phenyl-6-((2R,3R,4S,5R,6S)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-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:

: 124813-94-1
benzyl 2,3,6-tri-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-α-D-glucopyranoside

: 7189-69-7
N,N`-sulfuryldiimidazole

: 124813-95-2
Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-((2R,3R,4S,5R,6S)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at -30 ℃;
DOI:10.1016/0008-6215(89)84070-4

Reference yield:

: 97590-76-6
benzyl-O-β-D-glucopyranoside

: 124813-95-2
Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-((2R,3R,4S,5R,6S)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: NaOAc / 4 h / 110 °C

2: 69.3 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: ZnCl₂ / Ambient temperature

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

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium acetate; sodium hydride; zinc(II) chloride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(89)84070-4

Reference yield:

: 100-39-0
benzyl bromide

: 124813-95-2
Imidazole-1-sulfonic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-((2R,3R,4S,5R,6S)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH (60percent dispersion in oil); 2.) 60percent aq. acetic acid; 3.) 0.1M H₂SO₄ / 1.) DMF, 90 deg C, 2 h; 2.) 90 deg C, 2 h; 3.) 90 deg C, 2 h

2: NaOAc / 4 h / 110 °C

3: 69.3 percent / 1.) crushed molecular sieves (4 Angstroem); 2.) trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1.) r.t., 0.5 h; 2.) -20 deg C to r.t.

4: 1percent NaOMe / methanol / Ambient temperature

5: ZnCl₂ / Ambient temperature

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

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; sodium methylate; sodium acetate; sodium hydride; acetic acid; zinc(II) chloride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(89)84070-4