(1S,3S,4R,6R,7R,8R,9R)-7,9-Bis(benzyloxy)-8-hydroxy-4-(3-N-benzyloxymethylthymin-1-yl)-2,5-dioxatricyclo[4.2.1.0^3,7]nonane

Base Information

• Chemical Name: (1S,3S,4R,6R,7R,8R,9R)-7,9-Bis(benzyloxy)-8-hydroxy-4-(3-N-benzyloxymethylthymin-1-yl)-2,5-dioxatricyclo[4.2.1.0^3,7]nonane
• CAS No.: 383191-84-2
• Molecular Formula: C₃₄H₃₄N₂O₈
• Molecular Weight: 598.653

Synonyms:(1S,3S,4R,6R,7R,8R,9R)-7,9-Bis(benzyloxy)-8-hydroxy-4-(3-N-benzyloxymethylthymin-1-yl)-2,5-dioxatricyclo[4.2.1.0^3,7]nonane

Chemical Property of (1S,3S,4R,6R,7R,8R,9R)-7,9-Bis(benzyloxy)-8-hydroxy-4-(3-N-benzyloxymethylthymin-1-yl)-2,5-dioxatricyclo[4.2.1.0^3,7]nonane

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1S,3S,4R,6R,7R,8R,9R)-7,9-Bis(benzyloxy)-8-hydroxy-4-(3-N-benzyloxymethylthymin-1-yl)-2,5-dioxatricyclo[4.2.1.0^3,7]nonane

There total 5 articles about (1S,3S,4R,6R,7R,8R,9R)-7,9-Bis(benzyloxy)-8-hydroxy-4-(3-N-benzyloxymethylthymin-1-yl)-2,5-dioxatricyclo[4.2.1.0^3,7]nonane 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: 76.0%

Benzyloxymethyl chloride (3587-60-8) + (1R,3R,4S,5R,6R,7R,8R)-5,8-Bis(benzyloxy)-4,6-dihydroxy-3-(thymin-1-yl)-7-(4-tolylsulfonyloxy)-2-oxabicyclo[3.3.0]octane (383191-83-1) → (1S,3S,4R,6R,7R,8R,9R)-7,9-Bis(benzyloxy)-8-hydroxy-4-(3-N-benzyloxymethylthymin-1-yl)-2,5-dioxatricyclo[4.2.1.03,7]nonane (383191-84-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 22h;

DOI:10.1039/b104438a

Reference yield:

(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-hydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene (352422-92-5) → (1S,3S,4R,6R,7R,8R,9R)-7,9-Bis(benzyloxy)-8-hydroxy-4-(3-N-benzyloxymethylthymin-1-yl)-2,5-dioxatricyclo[4.2.1.03,7]nonane (383191-84-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / pyridine / 3 h / 20 °C

2: 85 percent / aq. NaOH / ethanol / 16 h / Heating

3: 83 percent / aq. OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 50 °C

4: 77 percent / pyridine / 48 h / 20 °C

5: 76 percent / DBU / acetonitrile / 22 h / 20 °C

With pyridine; sodium hydroxide; osmium(VIII) oxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; ethanol; acetonitrile; tert-butyl alcohol;

DOI:10.1039/b104438a

Reference yield:

(1R,3R,4S,5R,8R)-5,8-Bis(benzyloxy)-4-hydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene (383191-81-9) → (1S,3S,4R,6R,7R,8R,9R)-7,9-Bis(benzyloxy)-8-hydroxy-4-(3-N-benzyloxymethylthymin-1-yl)-2,5-dioxatricyclo[4.2.1.03,7]nonane (383191-84-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / aq. OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 50 °C

2: 77 percent / pyridine / 48 h / 20 °C

3: 76 percent / DBU / acetonitrile / 22 h / 20 °C

With pyridine; osmium(VIII) oxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; acetonitrile; tert-butyl alcohol;

DOI:10.1039/b104438a

upstream raw materials:

Benzyloxymethyl chloride

(1R,3R,4S,5R,6R,7R,8R)-5,8-Bis(benzyloxy)-4,6-dihydroxy-3-(thymin-1-yl)-7-(4-tolylsulfonyloxy)-2-oxabicyclo[3.3.0]octane

(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-hydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

(1R,3R,4S,5R,8R)-5,8-Bis(benzyloxy)-4-hydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

Downstream raw materials:

(1S,3S,4R,6R,7R,8R,9R)-8-Benzoyloxy-7,9-dihydroxy-4-(thymin-1-yl)-2,5-dioxatricyclo[4.2.1.0^3,7]nonane

(1S,3S,4R,6R,7R,8R,9R)-8-Benzoyloxy-9-(4,4'-dimethoxytrityloxy)-7-hydroxy-4-(thymin-1-yl)-2,5-dioxatricyclo[4.2.1.0^3,7]nonane

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