4-C-acetoxymethyl-5-O-acetyl-3-C-allyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

Base Information

• Chemical Name: 4-C-acetoxymethyl-5-O-acetyl-3-C-allyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose
• CAS No.: 485755-30-4
• Molecular Formula: C₂₃H₃₀O₈
• Molecular Weight: 434.486
• Mol file: 485755-30-4.mol

Synonyms:4-C-acetoxymethyl-5-O-acetyl-3-C-allyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

Chemical Property of 4-C-acetoxymethyl-5-O-acetyl-3-C-allyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-C-acetoxymethyl-5-O-acetyl-3-C-allyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

There total 5 articles about 4-C-acetoxymethyl-5-O-acetyl-3-C-allyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose 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: 85.0%

acetic anhydride (108-24-7) + 3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (457067-99-1) → 4-C-acetoxymethyl-5-O-acetyl-3-C-allyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (485755-30-4)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 12h;

DOI:10.1021/jo049159a

Reference yield:

3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (197702-06-0) → 4-C-acetoxymethyl-5-O-acetyl-3-C-allyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (485755-30-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: aq. acetic acid / methanol / 18 h

2.1: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

2.2: aq. NaOH / tetrahydrofuran; methanol / 12 h / 20 °C

2.3: 3.69 g / NaBH₄ / tetrahydrofuran; methanol / 1 h / 20 °C

3.1: 85 percent / pyridine; DMAP / 12 h / 20 °C

With pyridine; dmap; sodium periodate; acetic acid; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo049159a

Reference yield:

benzyl bromide (100-39-0) → 4-C-acetoxymethyl-5-O-acetyl-3-C-allyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (485755-30-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 95 percent / NaH / dimethylformamide / 3 h / 20 °C

2.1: aq. acetic acid / methanol / 18 h

3.1: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

3.2: aq. NaOH / tetrahydrofuran; methanol / 12 h / 20 °C

3.3: 3.69 g / NaBH₄ / tetrahydrofuran; methanol / 1 h / 20 °C

4.1: 85 percent / pyridine; DMAP / 12 h / 20 °C

With pyridine; dmap; sodium periodate; sodium hydride; acetic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo049159a

upstream raw materials:

acetic anhydride

3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

benzyl bromide

3-C-allyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Downstream raw materials:

Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-hydroxy-ethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-allyl-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

1-{(2R,3R,3aS,7aR)-3a-Benzyloxy-7a-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

1-(3-C-allyl-3-O-benzyl-4-C-tosyloxymethyl-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl)thymine