3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-(6S,7R)-dihydroxy-α-D-erythro-D-gluco-octa-1,4-furanose

Base Information

Chemical Name:3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-(6S,7R)-dihydroxy-α-D-erythro-D-gluco-octa-1,4-furanose
CAS No.:909705-88-0
Molecular Formula:C₂₅H₃₁NO₆
Molecular Weight:441.524
Hs Code.:

Synonyms:3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-(6S,7R)-dihydroxy-α-D-erythro-D-gluco-octa-1,4-furanose

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Chemical Property of 3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-(6S,7R)-dihydroxy-α-D-erythro-D-gluco-octa-1,4-furanose

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Technology Process of 3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-(6S,7R)-dihydroxy-α-D-erythro-D-gluco-octa-1,4-furanose

There total 5 articles about 3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-(6S,7R)-dihydroxy-α-D-erythro-D-gluco-octa-1,4-furanose 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: 64.0%

: 909705-87-9
(R)-1-benzyl-2-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2,5-dihydro-1H-pyrrole

: 909705-88-0
3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-(6S,7R)-dihydroxy-α-D-erythro-D-gluco-octa-1,4-furanose

Guidance literature:: With methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); potassium osmate(VI); Hydroquinone 1,4-phthalazinediyl diether; In water; tert-butyl alcohol; at 0 ℃; for 10h;
DOI:10.1021/jo060823s

Reference yield:

: C₂₂H₂₅NO₅

: 909705-88-0
3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-(6S,7R)-dihydroxy-α-D-erythro-D-gluco-octa-1,4-furanose

Guidance literature:: Multi-step reaction with 5 steps

1: 79 percent / TMSOTf / tetrahydrofuran; diethyl ether / 1 h / -78 °C

2: 88 percent / zinc; acetic acid; Cu(OAc)2 / H₂O / 1 h / 80 °C

3: 92 percent / anhydrous potassium carbonate / dimethylformamide / 12 h / 20 °C

4: 82 percent / Grubbs first generation catalyst / CH₂Cl₂ / 12 h / 20 °C

5: 64 percent / K₃Fe(CN)6; potassium carbonate; methanesulfonamide / K₂OsO₄*2H₂O; (DHQ)2PHAL / H₂O; 2-methyl-propan-2-ol / 10 h / 0 °C

With copper diacetate; methanesulfonamide; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; acetic acid; potassium hexacyanoferrate(III); zinc; potassium osmate(VI); Grubbs catalyst first generation; Hydroquinone 1,4-phthalazinediyl diether; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo060823s

Reference yield:

: 909705-86-8
(R)-N-allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-amine

: 909705-88-0
3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-(6S,7R)-dihydroxy-α-D-erythro-D-gluco-octa-1,4-furanose

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / Grubbs first generation catalyst / CH₂Cl₂ / 12 h / 20 °C

2: 64 percent / K₃Fe(CN)6; potassium carbonate; methanesulfonamide / K₂OsO₄*2H₂O; (DHQ)2PHAL / H₂O; 2-methyl-propan-2-ol / 10 h / 0 °C

With methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); potassium osmate(VI); Grubbs catalyst first generation; Hydroquinone 1,4-phthalazinediyl diether; In dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo060823s