Acetic acid (2S,3R,4S,6R)-4-acetoxy-2-[(1R,2S,3R,4R,5S,6R)-3,5-bis-(benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2S,3R,4S,6R)-4-acetoxy-2-[(1R,2S,3R,4R,5S,6R)-3,5-bis-(benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester
CAS No.:72212-15-8
Molecular Formula:C₃₄H₄₄N₂O₁₃
Molecular Weight:688.729
Hs Code.:

Acetic acid (2S,3R,4S,6R)-4-acetoxy-2-[(1R,2S,3R,4R,5S,6R)-3,5-bis-(benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2S,3R,4S,6R)-4-acetoxy-2-[(1R,2S,3R,4R,5S,6R)-3,5-bis-(benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,6R)-4-acetoxy-2-[(1R,2S,3R,4R,5S,6R)-3,5-bis-(benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester

There total 23 articles about Acetic acid (2S,3R,4S,6R)-4-acetoxy-2-[(1R,2S,3R,4R,5S,6R)-3,5-bis-(benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester 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%

: 64979-02-8
N,N'-<(benzyloxy)carbonyl>actinamine

: 72244-46-3
2,3-di-O-acetyl-4,6-dideoxy-α-D-xylo-hexopyranosyl chloride

: 72212-15-8,72244-47-4
Acetic acid (2S,3R,4S,6R)-4-acetoxy-2-[(1R,2S,3R,4R,5S,6R)-3,5-bis-(benzyloxycarbonyl-methyl-amino)-2,4,6-trihydroxy-cyclohexyloxy]-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With silver trifluoromethanesulfonate; In tetrahydrofuran; at -40 ℃;
DOI:10.1139/v85-026

Reference yield: 62.0%

: 72212-14-7
2,3-di-O-acetyl-4,6-dideoxy-α,β-D-ribo-hexopyranosyl chloride

: 64979-02-8
N,N'-<(benzyloxy)carbonyl>actinamine

: 72212-15-8,72244-47-4
4,4a-di-O-acetyl-N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin

Guidance literature:: silver trifluoromethanesulfonate; In tetrahydrofuran; at -40 ℃; for 3h;
DOI:10.1139/v85-026

Reference yield:

: 21736-83-4
(+)-spectinomycin dihydrochloride

: 72212-15-8,72244-47-4
4,4a-di-O-acetyl-N,N'-<(benzyloxy)carbonyl>-4(R),4a(R)-tetrahydrospectinomycin

Guidance literature:: Multi-step reaction with 5 steps

1: Dowex-1 (OH-)

2: H₂ / catalytic hydrogenation

3: 97 percent / pyridine / 18 h / 0 °C

4: 9 percent / silver carbonate / acetone; H₂O

5: 62 percent / silver trifluoromethanesulfonate / tetrahydrofuran / 3 h / -40 °C

With Dowex-1 (OH-); hydrogen; silver carbonate; silver trifluoromethanesulfonate; In tetrahydrofuran; pyridine; water; acetone;
DOI:10.1139/v85-026