(2R,3S,4S,5R,6R)-2-((1R)-1-((2S,5R)-4-acetoxy-5-(3-((benzyloxy)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methoxytetrahydrofuran-2-yl)-2-amino-2-oxoethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

Chemical Name:(2R,3S,4S,5R,6R)-2-((1R)-1-((2S,5R)-4-acetoxy-5-(3-((benzyloxy)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methoxytetrahydrofuran-2-yl)-2-amino-2-oxoethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
CAS No.:1158951-64-4
Molecular Formula:C₃₃H₄₁N₃O₁₇
Molecular Weight:751.698
Hs Code.:

(2R,3S,4S,5R,6R)-2-((1R)-1-((2S,5R)-4-acetoxy-5-(3-((benzyloxy)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methoxytetrahydrofuran-2-yl)-2-amino-2-oxoethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Synonyms:(2R,3S,4S,5R,6R)-2-((1R)-1-((2S,5R)-4-acetoxy-5-(3-((benzyloxy)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methoxytetrahydrofuran-2-yl)-2-amino-2-oxoethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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Chemical Property of (2R,3S,4S,5R,6R)-2-((1R)-1-((2S,5R)-4-acetoxy-5-(3-((benzyloxy)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methoxytetrahydrofuran-2-yl)-2-amino-2-oxoethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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Technology Process of (2R,3S,4S,5R,6R)-2-((1R)-1-((2S,5R)-4-acetoxy-5-(3-((benzyloxy)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methoxytetrahydrofuran-2-yl)-2-amino-2-oxoethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 10 articles about (2R,3S,4S,5R,6R)-2-((1R)-1-((2S,5R)-4-acetoxy-5-(3-((benzyloxy)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methoxytetrahydrofuran-2-yl)-2-amino-2-oxoethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 77.0%

: (2R,3S,4S,5R,6R)-2-((1R)-1-((2S,5R)-4-acetoxy-5-(3-((benzyloxy)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methoxytetrahydrofuran-2-yl)-2-amino-2-oxoethoxy)-6-((2-chloroacetoxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 1158951-64-4
(2R,3S,4S,5R,6R)-2-((1R)-1-((2S,5R)-4-acetoxy-5-(3-((benzyloxy)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methoxytetrahydrofuran-2-yl)-2-amino-2-oxoethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Guidance literature:: With thiourea; In tetrahydrofuran; methanol; at 50 ℃; for 14h; Inert atmosphere;
DOI:10.1021/acs.jmedchem.0c00545

Reference yield: 70.0%

: 1158951-59-7
C₃₅H₄₃N₃O₁₈

: 1158951-64-4
(2R,3S,4S,5R,6R)-2-((1R)-1-((2S,5R)-4-acetoxy-5-(3-((benzyloxy)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methoxytetrahydrofuran-2-yl)-2-amino-2-oxoethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Guidance literature:: With tetra-t-butyl-3-chloro-1-hydroxydistannoxane; In methanol; at 20 ℃; for 12h;
DOI:10.1021/ol900458w

Reference yield:

: 1158951-44-0
(2R,5R)-2-(3-((benzyloxy)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-(hydroxymethyl)-4-methoxytetrahydrofuran-3-yl acetate

: 1158951-64-4
(2R,3S,4S,5R,6R)-2-((1R)-1-((2S,5R)-4-acetoxy-5-(3-((benzyloxy)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methoxytetrahydrofuran-2-yl)-2-amino-2-oxoethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Guidance literature:: Multi-step reaction with 6 steps

1: diisopropyl-carbodiimide / dichloromethane; dimethyl sulfoxide / 2 h / 0 °C / Inert atmosphere

2: titanium(IV) isopropylate / dichloromethane; dimethyl sulfoxide; water / 8 h / 20 °C / Inert atmosphere

3: acetic acid / water / 12 h / 20 °C / Inert atmosphere

4: strontium(II) carbonate; silver tetrafluoroborate; N-iodo-succinimide / dichloromethane / 13 h / 0 °C / Molecular sieve; Inert atmosphere

5: mercury dichloride; Acetaldehyde oxime / water; ethanol / 14 h / 20 °C / Inert atmosphere

6: thiourea / tetrahydrofuran; methanol / 14 h / 50 °C / Inert atmosphere

With titanium(IV) isopropylate; strontium(II) carbonate; N-iodo-succinimide; silver tetrafluoroborate; Acetaldehyde oxime; acetic acid; thiourea; mercury dichloride; diisopropyl-carbodiimide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1021/acs.jmedchem.0c00545