benzyl 5-deoxy-5-azido-5-C-benzyloxymethyl-2,3-O-isopropylidene-α-D-manno-furanoside

Base Information

Chemical Name:benzyl 5-deoxy-5-azido-5-C-benzyloxymethyl-2,3-O-isopropylidene-α-D-manno-furanoside
CAS No.:1393474-10-6
Molecular Formula:C₂₄H₂₉N₃O₆
Molecular Weight:455.511
Hs Code.:

Synonyms:benzyl 5-deoxy-5-azido-5-C-benzyloxymethyl-2,3-O-isopropylidene-α-D-manno-furanoside

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Chemical Property of benzyl 5-deoxy-5-azido-5-C-benzyloxymethyl-2,3-O-isopropylidene-α-D-manno-furanoside

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Technology Process of benzyl 5-deoxy-5-azido-5-C-benzyloxymethyl-2,3-O-isopropylidene-α-D-manno-furanoside

There total 4 articles about benzyl 5-deoxy-5-azido-5-C-benzyloxymethyl-2,3-O-isopropylidene-α-D-manno-furanoside 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: 94.0%

: 1393474-09-3
benzyl-2,3-O-isopropylidene-5-deoxy-5-azido-5-C-benzyloxymethyl-α-L-gulo-furano-1,6-dialdose

: 1393474-10-6
benzyl 5-deoxy-5-azido-5-C-benzyloxymethyl-2,3-O-isopropylidene-α-D-manno-furanoside

Guidance literature:: With sodium tetrahydroborate; In methanol; for 3h; Cooling with ice; Inert atmosphere;
DOI:10.1021/jo3009534

Reference yield:

: benzyl 2,3-O-isopropylidene-6-O-benzyl-5-C-dichloromethyl-β-L-gulo-furanoside

: 1393474-10-6
benzyl 5-deoxy-5-azido-5-C-benzyloxymethyl-2,3-O-isopropylidene-α-D-manno-furanoside

Guidance literature:: Multi-step reaction with 2 steps

1: sodium azide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 4 h / Heating; Inert atmosphere

2: sodium tetrahydroborate / methanol / 3 h / Cooling with ice; Inert atmosphere

With sodium tetrahydroborate; sodium azide; tetra-(n-butyl)ammonium iodide; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo3009534

Reference yield:

: 1393474-05-9
benzyl 2,3-O-isopropylidene-6-O-benzyl-α-D-lyxo-hexofuranoside-5-ulose

: 1393474-10-6
benzyl 5-deoxy-5-azido-5-C-benzyloxymethyl-2,3-O-isopropylidene-α-D-manno-furanoside

Guidance literature:: Multi-step reaction with 3 steps

1: diisopropylamine; n-butyllithium / hexane / -78 - 30 °C / Inert atmosphere

2: sodium azide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 4 h / Heating; Inert atmosphere

3: sodium tetrahydroborate / methanol / 3 h / Cooling with ice; Inert atmosphere

With sodium tetrahydroborate; n-butyllithium; sodium azide; tetra-(n-butyl)ammonium iodide; diisopropylamine; In methanol; hexane; N,N-dimethyl-formamide;
DOI:10.1021/jo3009534