(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl (N,N-diisopropyl) phosphoramidite

Base Information

Chemical Name:(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl (N,N-diisopropyl) phosphoramidite
CAS No.:230620-32-3
Molecular Formula:C₃₇H₄₉N₂O₇P
Molecular Weight:664.779
Hs Code.:

Synonyms:(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl (N,N-diisopropyl) phosphoramidite

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Chemical Property of (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl (N,N-diisopropyl) phosphoramidite

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Technology Process of (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl (N,N-diisopropyl) phosphoramidite

There total 2 articles about (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl (N,N-diisopropyl) phosphoramidite 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: 83.0%

: 4356-80-3,34212-64-1,40653-32-5,53008-65-4,55094-38-7,68027-27-0,73111-53-2,128184-63-4,138794-99-7,641635-63-4
methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside

: 124482-92-4,89992-70-1
2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

: 230620-32-3
(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl (N,N-diisopropyl) phosphoramidite

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1139/v99-056

Reference yield:

: 67583-56-6
Methyl 2,3,4-O-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside

: 230620-32-3
(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl (N,N-diisopropyl) phosphoramidite

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / HBr / acetic acid / 0 °C

2: 83 percent / i-Pr₂NEt / CH₂Cl₂ / 0.5 h / 20 °C

With hydrogen bromide; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetic acid; 1: deprotection / 2: phosphorylation;
DOI:10.1139/v99-056

Reference yield:

: 230620-32-3
(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl (N,N-diisopropyl) phosphoramidite

: 230620-45-8
(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-L-ribityl-5-phosphate

Guidance literature:: Multi-step reaction with 3 steps

1: tetrazole / acetonitrile / 0.67 h

2: 84 percent / MCPBA / acetonitrile; CH₂Cl₂ / 0.33 h / 0 °C

3: 47 percent / 17 h / 20 °C

With 1H-tetrazole; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile; 1: glycosylation / 2: Oxidation / 3: Condensation;
DOI:10.1139/v99-056