alpha-D-erythro-Pentofuranoside,methyl2-deoxy-2-methylene-(9CI)

Base Information

• Chemical Name: alpha-D-erythro-Pentofuranoside,methyl2-deoxy-2-methylene-(9CI)
• CAS No.: 229469-30-1
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.17
• Mol file: 229469-30-1.mol

Synonyms:alpha-D-erythro-Pentofuranoside,methyl2-deoxy-2-methylene-(9CI)

Chemical Property of alpha-D-erythro-Pentofuranoside,methyl2-deoxy-2-methylene-(9CI)

Chemical Property:

• PSA: 58.92000
• LogP: -0.73290

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of alpha-D-erythro-Pentofuranoside,methyl2-deoxy-2-methylene-(9CI)

There total 7 articles about alpha-D-erythro-Pentofuranoside,methyl2-deoxy-2-methylene-(9CI) 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: 100.0%

2,2-di-tert-butyl-6-methoxy-7-methylene-tetrahydro-furo[3,2-d][1,3,2]dioxasiline (232944-89-7) → (2R,3S,5S)-2-Hydroxymethyl-5-methoxy-4-methylene-tetrahydro-furan-3-ol (229469-30-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1080/15257779908041488

Reference yield: 88.0%

2-deoxy-2-methylene-1-α-methyl-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-D-ribofuranose (229469-29-8) → (2R,3S,5S)-2-Hydroxymethyl-5-methoxy-4-methylene-tetrahydro-furan-3-ol (229469-30-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(99)00394-4

Reference yield:

methyl D-arabinofuranoside (56607-40-0) → (2R,3S,5S)-2-Hydroxymethyl-5-methoxy-4-methylene-tetrahydro-furan-3-ol (229469-30-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / DMAP / pyridine / 12 h / 20 °C

2: DCC, DMSO, TFA / pyridine / 16 h / 20 °C

3: 56 percent / diethyl ether / 1 h / -10 °C

4: 100 percent / TBAF / tetrahydrofuran / 48 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; diethyl ether; 1: Substitution / 2: Oxidation / 3: Wittig reaction / 4: desilylation;

DOI:10.1080/15257779908041488

upstream raw materials:

2-deoxy-2-methylene-1-α-methyl-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-D-ribofuranose

2,2-di-tert-butyl-6-methoxy-7-methylene-tetrahydro-furo[3,2-d][1,3,2]dioxasiline

methyl D-arabinofuranoside

methyl 3,5-O-(di-tert-butylsilylene)-α-D-arabinofuranoside

Downstream raw materials:

3-O-benzyl-2-deoxy-2-(4,4'-dimethoxytriryloxymethyl)-4-C-hydroxymethyl-1-α-methyl-D-ribofuranose

(1R,3R,4R,8S)-1-acetoxymethyl-3-(N²-acetylguanin-9-yl)-8-benzyloxy-2,6-dioxabicyclo<3.2.1>octane

(1R,3S,4R,8S)-1-acetoxymethyl-3-(N²-acetylguanin-9-yl)-8-benzyloxy-2,6-dioxabicyclo<3.2.1>octane

(1R,3S,4R,8S)-1-acetoxymethyl-3-(N²-acetylguanin-7-yl)-8-benzyloxy-2,6-dioxabicyclo<3.2.1>octane

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