4-O-Benzyl-6,7-O-trifluoromethylsulfonyl-D-glycero-D-gulo-heptono-1,5-lactone

Base Information

• Chemical Name: 4-O-Benzyl-6,7-O-trifluoromethylsulfonyl-D-glycero-D-gulo-heptono-1,5-lactone
• CAS No.: 145372-87-8
• Molecular Formula: C₁₈H₂₁F₃O₉S
• Molecular Weight: 470.421

Synonyms:4-O-Benzyl-6,7-O-trifluoromethylsulfonyl-D-glycero-D-gulo-heptono-1,5-lactone

Chemical Property of 4-O-Benzyl-6,7-O-trifluoromethylsulfonyl-D-glycero-D-gulo-heptono-1,5-lactone

Chemical Property:

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Technology Process of 4-O-Benzyl-6,7-O-trifluoromethylsulfonyl-D-glycero-D-gulo-heptono-1,5-lactone

There total 1 articles about 4-O-Benzyl-6,7-O-trifluoromethylsulfonyl-D-glycero-D-gulo-heptono-1,5-lactone 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: 67.0%

trifluoromethylsulfonic anhydride (358-23-6) + 4-O-benzyl-6,7-O-isopropylidene-D-glycero-D-gulo-heptono-1,5-lactone (34360-69-5) → 4-O-Benzyl-6,7-O-trifluoromethylsulfonyl-D-glycero-D-gulo-heptono-1,5-lactone (145372-87-8)

Guidance literature:

With pyridine; In dichloromethane; at -30 ℃; for 0.0833333h;

DOI:10.1039/p19960002151

Reference yield: 93.0%

methanol (67-56-1) + 4-O-Benzyl-6,7-O-trifluoromethylsulfonyl-D-glycero-D-gulo-heptono-1,5-lactone (145372-87-8) → Methyl 2,5-anhydro-4-O-benzyl-D-glycero-D-ido-heptonate (152389-09-8)

Guidance literature:

With hydrogenchloride; for 2h; Ambient temperature;

DOI:10.1039/c39930001065

Reference yield: 33.0%

4-O-Benzyl-6,7-O-trifluoromethylsulfonyl-D-glycero-D-gulo-heptono-1,5-lactone (145372-87-8) → (3S,4S,5R,6R)-3-Azido-5-benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-tetrahydro-pyran-2-one (164665-85-4) + (3R,4S,5R,6R)-3-Azido-5-benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-tetrahydro-pyran-2-one (164665-84-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)00198-L

upstream raw materials:

trifluoromethylsulfonic anhydride

4-O-benzyl-6,7-O-isopropylidene-D-glycero-D-gulo-heptono-1,5-lactone

Downstream raw materials:

Methyl 2,5-anhydro-4-O-benzyl-6,7-O-isopropylidene-D-glycero-D-ido-heptonate

Methyl 2,5-anhydro-4-O-benzyl-D-glycero-D-ido-heptonate

(2S,3R,4R,5R)-4-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-tetrahydro-furan-2-carboxylic acid benzylamide

(3S,4S,5R,6R)-3-Azido-5-benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-tetrahydro-pyran-2-one

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