Acetic acid (3R,4S,5R)-4-azido-5-[(6-benzoylamino-purin-9-yl)-methoxy-methyl]-3-trimethylsilanyloxy-tetrahydro-furan-3-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (3R,4S,5R)-4-azido-5-[(6-benzoylamino-purin-9-yl)-methoxy-methyl]-3-trimethylsilanyloxy-tetrahydro-furan-3-ylmethyl ester
• CAS No.: 345235-45-2
• Molecular Formula: C₂₄H₃₀N₈O₆Si
• Molecular Weight: 554.638
• Mol file: 345235-45-2.mol

Synonyms:

Chemical Property of Acetic acid (3R,4S,5R)-4-azido-5-[(6-benzoylamino-purin-9-yl)-methoxy-methyl]-3-trimethylsilanyloxy-tetrahydro-furan-3-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (3R,4S,5R)-4-azido-5-[(6-benzoylamino-purin-9-yl)-methoxy-methyl]-3-trimethylsilanyloxy-tetrahydro-furan-3-ylmethyl ester

There total 6 articles about Acetic acid (3R,4S,5R)-4-azido-5-[(6-benzoylamino-purin-9-yl)-methoxy-methyl]-3-trimethylsilanyloxy-tetrahydro-furan-3-ylmethyl 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:

3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (153914-98-8) → Acetic acid (3R,4S,5R)-4-azido-5-[(6-benzoylamino-purin-9-yl)-methoxy-methyl]-3-trimethylsilanyloxy-tetrahydro-furan-3-ylmethyl ester (345235-45-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 94 percent / NaOMe / methanol / 1 h / 20 °C

2.1: pyridine / 1.5 h / 20 °C

3.1: 5.16 g / aq. HCl / 72 h / 20 °C

4.1: aq. NaOH / dioxane / 1 h / 20 °C

5.1: 2.40 g / aq. NaOH / dioxane / 96 h / 85 °C

6.1: pyridine / 5 h / 20 °C

7.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / Heating

7.2: 74.0 mg / acetonitrile / 90 h / 70 °C

With pyridine; hydrogenchloride; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; sodium methylate; In 1,4-dioxane; methanol; acetonitrile;

DOI:10.1039/b009109j

Reference yield:

3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (247025-10-1) → Acetic acid (3R,4S,5R)-4-azido-5-[(6-benzoylamino-purin-9-yl)-methoxy-methyl]-3-trimethylsilanyloxy-tetrahydro-furan-3-ylmethyl ester (345235-45-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / 1.5 h / 20 °C

2.1: 5.16 g / aq. HCl / 72 h / 20 °C

3.1: aq. NaOH / dioxane / 1 h / 20 °C

4.1: 2.40 g / aq. NaOH / dioxane / 96 h / 85 °C

5.1: pyridine / 5 h / 20 °C

6.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / Heating

6.2: 74.0 mg / acetonitrile / 90 h / 70 °C

With pyridine; hydrogenchloride; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; In 1,4-dioxane; acetonitrile;

DOI:10.1039/b009109j

Reference yield:

Methyl 3-azido-3-deoxy-2-O,4-C-methylene-D-ribofuranoside (345235-42-9) → Acetic acid (3R,4S,5R)-4-azido-5-[(6-benzoylamino-purin-9-yl)-methoxy-methyl]-3-trimethylsilanyloxy-tetrahydro-furan-3-ylmethyl ester (345235-45-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / 5 h / 20 °C

2.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / Heating

2.2: 74.0 mg / acetonitrile / 90 h / 70 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile;

DOI:10.1039/b009109j

upstream raw materials:

3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

Methyl 3-azido-3-deoxy-2-O,4-C-methylene-D-ribofuranoside

Methyl 3-azido-3-deoxy-5-O-mesyl-4-C-mesyloxymethyl-D-erythro-pentofuranose