7-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-methyl-chromen-2-one

Base Information

Chemical Name:7-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-methyl-chromen-2-one
CAS No.:172364-23-7
Molecular Formula:C₂₉H₃₄O₁₃
Molecular Weight:590.581
Hs Code.:

7-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-methyl-chromen-2-one

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Chemical Property of 7-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-methyl-chromen-2-one

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Technology Process of 7-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-methyl-chromen-2-one

There total 9 articles about 7-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-methyl-chromen-2-one 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:

: 604-68-2
α-D-glucopyranose peracetylate

: 172364-23-7
7-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-methyl-chromen-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: HBr / acetic acid / Ambient temperature

2: 71 percent / HgBr₂, Hg(CN)2, molecular sieve 4Ae / CH₂Cl₂ / 17 h

3: 60percent aq. AcOH / 0.75 h / Heating

4: 20mM methanolic MeONa / 15 h / Ambient temperature

With 4 A molecular sieve; hydrogen bromide; sodium methylate; mercury(II) cyanide; acetic acid; mercury dibromide; In dichloromethane; acetic acid;
DOI:10.1016/0008-6215(95)00102-Y

Reference yield:

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 172364-23-7
7-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-methyl-chromen-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 71 percent / HgBr₂, Hg(CN)2, molecular sieve 4Ae / CH₂Cl₂ / 17 h

2: 60percent aq. AcOH / 0.75 h / Heating

3: 20mM methanolic MeONa / 15 h / Ambient temperature

With 4 A molecular sieve; sodium methylate; mercury(II) cyanide; acetic acid; mercury dibromide; In dichloromethane;
DOI:10.1016/0008-6215(95)00102-Y

Reference yield:

: 90-33-5,79566-13-5
7-hydroxy-4-methyl-chromen-2-one

: 172364-23-7
7-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-methyl-chromen-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 43 percent / aq. NaOH / acetone / 7 h / Ambient temperature

2: 6mM methanolic MeONa / 5 h / Ambient temperature

3: 95 percent / 10-camphorsulfonic acid / benzene / 12 h / Heating

4: 47 percent / tetrabutylammonium hydrogen sulfate, 5percent aq. NaOH / CH₂Cl₂ / 24 h / Heating

5: 42 percent / molecular sieve 4Ae, methyl trifluoromethanesulfonate / CH₂Cl₂ / 44 h

6: 60percent aq. AcOH / 0.75 h / Heating

7: 20mM methanolic MeONa / 15 h / Ambient temperature

With sodium hydroxide; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; acetic acid; methyl trifluoromethanesulfonate; In dichloromethane; acetone; benzene;
DOI:10.1016/0008-6215(95)00102-Y