(4S,5R,6R,7R,8R)-5-Acetylamino-4,7,8,9-tetrahydroxy-6-(4-methoxy-benzyloxy)-2-methylene-nonanoic acid tert-butyl ester

Base Information

Chemical Name:(4S,5R,6R,7R,8R)-5-Acetylamino-4,7,8,9-tetrahydroxy-6-(4-methoxy-benzyloxy)-2-methylene-nonanoic acid tert-butyl ester
CAS No.:212752-13-1
Molecular Formula:C₂₄H₃₇NO₉
Molecular Weight:483.559
Hs Code.:

Synonyms:(4S,5R,6R,7R,8R)-5-Acetylamino-4,7,8,9-tetrahydroxy-6-(4-methoxy-benzyloxy)-2-methylene-nonanoic acid tert-butyl ester

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Chemical Property of (4S,5R,6R,7R,8R)-5-Acetylamino-4,7,8,9-tetrahydroxy-6-(4-methoxy-benzyloxy)-2-methylene-nonanoic acid tert-butyl ester

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Technology Process of (4S,5R,6R,7R,8R)-5-Acetylamino-4,7,8,9-tetrahydroxy-6-(4-methoxy-benzyloxy)-2-methylene-nonanoic acid tert-butyl ester

There total 6 articles about (4S,5R,6R,7R,8R)-5-Acetylamino-4,7,8,9-tetrahydroxy-6-(4-methoxy-benzyloxy)-2-methylene-nonanoic acid tert-butyl 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: 70.0%

: 53913-96-5
tert-butyl 2-(bromomethyl)acrylate

: N-[(3S,4R,5S,6R)-2,5-Dihydroxy-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide

: 212752-13-1
(4S,5R,6R,7R,8R)-5-Acetylamino-4,7,8,9-tetrahydroxy-6-(4-methoxy-benzyloxy)-2-methylene-nonanoic acid tert-butyl ester

Guidance literature:: With hydrogenchloride; indium; water; tetra-(n-butyl)ammonium iodide; In acetonitrile; at 40 ℃;
DOI:10.1002/(SICI)1521-3773(19980703)37:12<1732::AID-ANIE1732>3.0.CO;2-I

Reference yield:

: 72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4
N-acetyl-β-D-mannosamine

: 212752-13-1
(4S,5R,6R,7R,8R)-5-Acetylamino-4,7,8,9-tetrahydroxy-6-(4-methoxy-benzyloxy)-2-methylene-nonanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / BF₃*Et₂O / 95 °C

2: 70 percent / p-TsOH / acetonitrile / 0 °C

3: 88 percent / CF₃SO₃H / tetrahydrofuran; diethyl ether / 0 °C

4: HCO₂H, Et₃N / Pd(PPh₃)4 / dioxane / 65 - 95 °C

5: AcOH / Ambient temperature

6: 70 percent / In, TBAI, H₂O, HCl / acetonitrile / 40 °C

With hydrogenchloride; indium; formic acid; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; water; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; acetic acid; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; diethyl ether; acetonitrile;
DOI:10.1002/(SICI)1521-3773(19980703)37:12<1732::AID-ANIE1732>3.0.CO;2-I

Reference yield:

: N-[(4aR,7S,8R,8aS)-6-Allyloxy-8-hydroxy-2-(4-methoxy-benzyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

: 212752-13-1
(4S,5R,6R,7R,8R)-5-Acetylamino-4,7,8,9-tetrahydroxy-6-(4-methoxy-benzyloxy)-2-methylene-nonanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / CF₃SO₃H / tetrahydrofuran; diethyl ether / 0 °C

2: HCO₂H, Et₃N / Pd(PPh₃)4 / dioxane / 65 - 95 °C

3: AcOH / Ambient temperature

4: 70 percent / In, TBAI, H₂O, HCl / acetonitrile / 40 °C

With hydrogenchloride; indium; formic acid; trifluorormethanesulfonic acid; water; tetra-(n-butyl)ammonium iodide; acetic acid; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; diethyl ether; acetonitrile;
DOI:10.1002/(SICI)1521-3773(19980703)37:12<1732::AID-ANIE1732>3.0.CO;2-I