methyl 6-deoxy-5-O-(phenylmethyl)-L-glycero-α-D-allo-octofuranuronate 1,2,3-triacetate 7-methanesulfonate

Base Information

Chemical Name:methyl 6-deoxy-5-O-(phenylmethyl)-L-glycero-α-D-allo-octofuranuronate 1,2,3-triacetate 7-methanesulfonate
CAS No.:101696-58-6
Molecular Formula:C₂₃H₃₀O₁₃S
Molecular Weight:546.549
Hs Code.:

Synonyms:methyl 6-deoxy-5-O-(phenylmethyl)-L-glycero-α-D-allo-octofuranuronate 1,2,3-triacetate 7-methanesulfonate

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Chemical Property of methyl 6-deoxy-5-O-(phenylmethyl)-L-glycero-α-D-allo-octofuranuronate 1,2,3-triacetate 7-methanesulfonate

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Technology Process of methyl 6-deoxy-5-O-(phenylmethyl)-L-glycero-α-D-allo-octofuranuronate 1,2,3-triacetate 7-methanesulfonate

There total 13 articles about methyl 6-deoxy-5-O-(phenylmethyl)-L-glycero-α-D-allo-octofuranuronate 1,2,3-triacetate 7-methanesulfonate 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:

: 108-24-7
acetic anhydride

: (2R,4R)-4-Benzyloxy-4-((2R,3R,4R)-3,4-diacetoxy-5-methoxy-tetrahydro-furan-2-yl)-2-methanesulfonyloxy-butyric acid methyl ester

: 101696-58-6
methyl 6-deoxy-5-O-(phenylmethyl)-L-glycero-α-D-allo-octofuranuronate 1,2,3-triacetate 7-methanesulfonate

: 101696-59-7
methyl 6-deoxy-5-O-(phenylmethyl)-L-glycero-β-D-allo-octofuranuronate 1,2,3-triacetate 7-methanesulfonate

Guidance literature:: With sulfuric acid; acetic acid; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ja00230a024

Reference yield:

: 33985-40-9
(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

: 101696-58-6
methyl 6-deoxy-5-O-(phenylmethyl)-L-glycero-α-D-allo-octofuranuronate 1,2,3-triacetate 7-methanesulfonate

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) zinc chloride, 2.) trifluoroacetic acid / 1.) THF, r.t., 9 h, 2.) r.t., 3 h

2: 11.5 g / CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -78 °C

3: 13.5 g / 50 percent NaH / dimethylformamide; paraffin / 0 °C

4: 1.) NaIO₄, OsO₄, 2.) 5 percent aq. K₂CO₃ / 1.) dioxane/H₂O, r.t., overnight, 2.) MeOH, r.t., 1 h

5: 86 percent / Ag₂CO₃-Celite / xylene / 1.5 h / Heating

6: lithium hydroxide monohydrate, H₂O / 1,2-dimethoxy-ethane / 2 h / 50 °C

7: 1.) 50 percent NaH, 2.) 1 N HCl / dimethylformamide; paraffin

8: diethyl ether; methanol

9: 62 percent / DDQ, H₂O / CH₂Cl₂ / 24 h

10: 83 percent / triethylamine / CH₂Cl₂ / 1.) -20 deg C, 3 h, 2.) 0 deg C, 3 h

11: 1 N HCl / methanol / 1.5 h / Heating

12: 248 mg / pyridine / 5 h

13: 38 mg / acetic acid, conc. H₂SO₄ / CH₂Cl₂ / 1 h / 0 °C

With pyridine; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; cerium(III) chloride; sulfuric acid; water; sodium hydride; potassium carbonate; acetic acid; triethylamine; silver carbonate; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; paraffin; xylene;
DOI:10.1021/ja00230a024

Reference yield:

: 99441-05-1
methyl 5,9-anhydro-6,8-dideoxy-2,3-O-(1-methylethylidene)-β-D-allo-non-8-enofuranosid-7-ulose

: 101696-58-6
methyl 6-deoxy-5-O-(phenylmethyl)-L-glycero-α-D-allo-octofuranuronate 1,2,3-triacetate 7-methanesulfonate

Guidance literature:: Multi-step reaction with 12 steps

1: 11.5 g / CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -78 °C

2: 13.5 g / 50 percent NaH / dimethylformamide; paraffin / 0 °C

3: 1.) NaIO₄, OsO₄, 2.) 5 percent aq. K₂CO₃ / 1.) dioxane/H₂O, r.t., overnight, 2.) MeOH, r.t., 1 h

4: 86 percent / Ag₂CO₃-Celite / xylene / 1.5 h / Heating

5: lithium hydroxide monohydrate, H₂O / 1,2-dimethoxy-ethane / 2 h / 50 °C

6: 1.) 50 percent NaH, 2.) 1 N HCl / dimethylformamide; paraffin

7: diethyl ether; methanol

8: 62 percent / DDQ, H₂O / CH₂Cl₂ / 24 h

9: 83 percent / triethylamine / CH₂Cl₂ / 1.) -20 deg C, 3 h, 2.) 0 deg C, 3 h

10: 1 N HCl / methanol / 1.5 h / Heating

11: 248 mg / pyridine / 5 h

12: 38 mg / acetic acid, conc. H₂SO₄ / CH₂Cl₂ / 1 h / 0 °C

With pyridine; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; cerium(III) chloride; sulfuric acid; water; sodium hydride; potassium carbonate; acetic acid; triethylamine; silver carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; paraffin; xylene;
DOI:10.1021/ja00230a024