(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-methyl-4-N-benzoylcytosine-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-methyl-4-N-benzoylcytosine-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:206055-81-4
Molecular Formula:C₁₈H₁₉N₃O₆
Molecular Weight:373.365
Hs Code.:

Synonyms:(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-methyl-4-N-benzoylcytosine-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Suppliers and Price of (1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-methyl-4-N-benzoylcytosine-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-methyl-4-N-benzoylcytosine-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:: 99%, ^*data from raw suppliers

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Technology Process of (1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-methyl-4-N-benzoylcytosine-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

There total 11 articles about (1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-methyl-4-N-benzoylcytosine-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 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: 65.0%

: N-[1-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]-5-methyl-2-oxopyrimidin-4-yl]benzamide

: 206055-81-4
(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-methyl-4-N-benzoylcytosine-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: With trichloroacetic acid; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1080/15257770701571693

Reference yield:

: 63593-03-3
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

: 206055-81-4
(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-methyl-4-N-benzoylcytosine-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) NaH / 1.) DMF, -5 deg C, 1.5 h, 2.) room temperature, 3 h

2: 90 percent / pyridine / 3 h / Ambient temperature

3: 80percent AcOH / 4 h / 90 °C

4: pyridine / 72 h / Ambient temperature

5: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TMS-triflate / 1.) CH₃CN, reflux, 1 h, 2.) 65 deg C, 2 h

6: 97 percent / NaOMe / methanol / 0.17 h / Ambient temperature

7: 1.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h

8: 98 percent / H₂ / Pd(OH)2/C / ethanol / 4 h / Ambient temperature

9: 90 percent / DMAP / pyridine / 2 h

With dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; sodium hydride; acetic acid; p-toluenesulfonyl chloride; palladium dihydroxide; In pyridine; methanol; ethanol;
DOI:10.1016/S0040-4020(98)00094-5

Reference yield:

: 153186-10-8
((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

: 206055-81-4
(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-methyl-4-N-benzoylcytosine-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / pyridine / 3 h / Ambient temperature

2: 80percent AcOH / 4 h / 90 °C

3: pyridine / 72 h / Ambient temperature

4: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TMS-triflate / 1.) CH₃CN, reflux, 1 h, 2.) 65 deg C, 2 h

5: 97 percent / NaOMe / methanol / 0.17 h / Ambient temperature

6: 1.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h

7: 98 percent / H₂ / Pd(OH)2/C / ethanol / 4 h / Ambient temperature

8: 90 percent / DMAP / pyridine / 2 h

With dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; sodium hydride; acetic acid; p-toluenesulfonyl chloride; palladium dihydroxide; In pyridine; methanol; ethanol;
DOI:10.1016/S0040-4020(98)00094-5