methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate

Base Information

Chemical Name:methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate
CAS No.:347838-08-8
Molecular Formula:C₃₂H₄₄NO₁₆PSe
Molecular Weight:808.632
Hs Code.:

methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate

Synonyms:methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate

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Chemical Property of methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate

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Technology Process of methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate

There total 4 articles about methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate 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: 85.0%

: 589-57-1
diethyl phosphorylchloridite

: 347838-06-6
methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate

: 347838-08-8
methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 3h;
DOI:10.1016/S0008-6215(01)00029-5

Reference yield:

: 5707-04-0
Phenylselenyl chloride

: 347838-08-8
methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate

Guidance literature:: Multi-step reaction with 3 steps

1: 51 percent / AgOTf; H₂O / tetrahydrofuran / 168 h / 2 °C

2: 66 percent / p-TsOH*H₂O / 14 h / 65 °C

3: 85 percent / EtN(i-Pr)2 / acetonitrile / 3 h

With water; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetonitrile;
DOI:10.1016/S0008-6215(01)00029-5

Reference yield:

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 347838-08-8
methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate

Guidance literature:: Multi-step reaction with 3 steps

1: 51 percent / AgOTf; H₂O / tetrahydrofuran / 168 h / 2 °C

2: 66 percent / p-TsOH*H₂O / 14 h / 65 °C

3: 85 percent / EtN(i-Pr)2 / acetonitrile / 3 h

With water; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetonitrile;
DOI:10.1016/S0008-6215(01)00029-5