ethyl 1,7-dideoxy-6-c-carbethoxy-3,6-anhydro-1-(6-N-benzoylamino-9H-purin-9-yl)-2,5-diacetoxy-α-D-gluco-oct-1,4-furanuronate

Base Information

• Chemical Name: ethyl 1,7-dideoxy-6-c-carbethoxy-3,6-anhydro-1-(6-N-benzoylamino-9H-purin-9-yl)-2,5-diacetoxy-α-D-gluco-oct-1,4-furanuronate
• CAS No.: 544695-77-4
• Molecular Formula: C₂₉H₃₁N₅O₁₁
• Molecular Weight: 625.592
• Mol file: 544695-77-4.mol

Synonyms:ethyl 1,7-dideoxy-6-c-carbethoxy-3,6-anhydro-1-(6-N-benzoylamino-9H-purin-9-yl)-2,5-diacetoxy-α-D-gluco-oct-1,4-furanuronate

Chemical Property of ethyl 1,7-dideoxy-6-c-carbethoxy-3,6-anhydro-1-(6-N-benzoylamino-9H-purin-9-yl)-2,5-diacetoxy-α-D-gluco-oct-1,4-furanuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 1,7-dideoxy-6-c-carbethoxy-3,6-anhydro-1-(6-N-benzoylamino-9H-purin-9-yl)-2,5-diacetoxy-α-D-gluco-oct-1,4-furanuronate

There total 11 articles about ethyl 1,7-dideoxy-6-c-carbethoxy-3,6-anhydro-1-(6-N-benzoylamino-9H-purin-9-yl)-2,5-diacetoxy-α-D-gluco-oct-1,4-furanuronate 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: 73.0%

N-Benzoyl-N,9-bis(trimethylsilyl)adenin (18055-47-5) + ethyl 3,6-anhydro-6-(R)-carbethoxy-7-deoxy-1,2,5-O-triacetoxy-α-D-gluco-oct-1,4-furanuronate (544695-76-3) → ethyl 1,7-dideoxy-6-c-carbethoxy-3,6-anhydro-1-(6-N-benzoylamino-9H-purin-9-yl)-2,5-diacetoxy-α-D-gluco-oct-1,4-furanuronate (544695-77-4)

Guidance literature:

With t-butyldimethylsiyl triflate; In acetonitrile; at 75 ℃; for 3h;

DOI:10.1021/jo026858j

Reference yield:

1,2:5,6-diacetone-D-glucose (582-52-5) → ethyl 1,7-dideoxy-6-c-carbethoxy-3,6-anhydro-1-(6-N-benzoylamino-9H-purin-9-yl)-2,5-diacetoxy-α-D-gluco-oct-1,4-furanuronate (544695-77-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran / 6 h / 25 °C

1.2: 78 percent / TBAI / tetrahydrofuran / 12 h / 25 °C

2.1: 89 percent / H₂SO₄ / ethanol; H₂O / 6 h / 25 °C

3.1: 86 percent / sodium metaperiodate / acetone; H₂O / 2 h / 0 °C

4.1: 76 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / 0 °C

5.1: 83 percent / triethylamine; methanesulfonyl azide / acetonitrile / 2.5 h / 25 °C

6.1: 74 percent / Rh₂(OAc)4 / benzene / 0.17 h / 80 °C

7.1: 89 percent / sodium borohydride / methanol / 2 h / 0 °C

8.1: 94 percent / pyridine; 4-N,N-dimethylaminopyridine / 12 h / 25 °C

9.1: 59 percent / acetic acid; H₂SO₄ / CH₂Cl₂ / 4 h / 25 °C

10.1: 73 percent / tert-butyl(dimethyl)silyl triflate / acetonitrile / 3 h / 75 °C

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; sulfuric acid; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; sodium hydride; acetic acid; triethylamine; Methanesulfonyl azide; dirhodium tetraacetate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; acetonitrile; benzene; 10.1: Vorbrueggen glycosylation;

DOI:10.1021/jo026858j

Reference yield:

D-glucose (50-99-7) → ethyl 1,7-dideoxy-6-c-carbethoxy-3,6-anhydro-1-(6-N-benzoylamino-9H-purin-9-yl)-2,5-diacetoxy-α-D-gluco-oct-1,4-furanuronate (544695-77-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 72 percent / I₂ / 6 h / 25 °C

2.1: NaH / tetrahydrofuran / 6 h / 25 °C

2.2: 78 percent / TBAI / tetrahydrofuran / 12 h / 25 °C

3.1: 89 percent / H₂SO₄ / ethanol; H₂O / 6 h / 25 °C

4.1: 86 percent / sodium metaperiodate / acetone; H₂O / 2 h / 0 °C

5.1: 76 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / 0 °C

6.1: 83 percent / triethylamine; methanesulfonyl azide / acetonitrile / 2.5 h / 25 °C

7.1: 74 percent / Rh₂(OAc)4 / benzene / 0.17 h / 80 °C

8.1: 89 percent / sodium borohydride / methanol / 2 h / 0 °C

9.1: 94 percent / pyridine; 4-N,N-dimethylaminopyridine / 12 h / 25 °C

10.1: 59 percent / acetic acid; H₂SO₄ / CH₂Cl₂ / 4 h / 25 °C

11.1: 73 percent / tert-butyl(dimethyl)silyl triflate / acetonitrile / 3 h / 75 °C

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; sulfuric acid; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; iodine; sodium hydride; acetic acid; triethylamine; Methanesulfonyl azide; dirhodium tetraacetate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; acetonitrile; benzene; 11.1: Vorbrueggen glycosylation;

DOI:10.1021/jo026858j

upstream raw materials:

N-Benzoyl-N,9-bis(trimethylsilyl)adenin

ethyl 3,6-anhydro-6-(R)-carbethoxy-7-deoxy-1,2,5-O-triacetoxy-α-D-gluco-oct-1,4-furanuronate

1,2:5,6-diacetone-D-glucose

D-glucose