5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-1-O-methyl-D-ribofuranoside

Base Information

• Chemical Name: 5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-1-O-methyl-D-ribofuranoside
• CAS No.: 871578-68-6
• Molecular Formula: C₂₁H₂₆O₅
• Molecular Weight: 358.434
• Mol file: 871578-68-6.mol

Synonyms:5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-1-O-methyl-D-ribofuranoside

Chemical Property of 5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-1-O-methyl-D-ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-1-O-methyl-D-ribofuranoside

There total 1 articles about 5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-1-O-methyl-D-ribofuranoside 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: 94.0%

3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose (69827-91-4) → 5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-1-O-methyl-D-ribofuranoside (871578-68-6)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 1.5h;

DOI:10.1080/00397910500213864

Reference yield:

5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-1-O-methyl-D-ribofuranoside (871578-68-6) → (2'R,3'S,4'R)-1-(2',3'-di-benzyloxymethyl-tetrahydrofuran-4'-yl)-3-methoxycarbonyl-1,2,4-triazole (871578-72-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ammonium sulfate; hexamethyldisilazane / 2 h / Heating

1.2: 88 percent / triethylsilane; trimethylsilyl triflate / CH₂Cl₂ / 1.5 h / 20 °C

2.1: 96 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 18 h / 20 °C

3.1: 55 percent / NaH / dimethylformamide / 20 - 75 °C

With dmap; ammonium sulfate; sodium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/00397910500213864

Reference yield:

5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-1-O-methyl-D-ribofuranoside (871578-68-6) → (2'R,3'S,4'R)-1-(2',3'-di-benzyloxymethyl-tetrahydrofuran-4'-yl)-3-aminocarbonyl-1,2,4-triazole (871578-74-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ammonium sulfate; hexamethyldisilazane / 2 h / Heating

1.2: 88 percent / triethylsilane; trimethylsilyl triflate / CH₂Cl₂ / 1.5 h / 20 °C

2.1: 96 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 18 h / 20 °C

3.1: 55 percent / NaH / dimethylformamide / 20 - 75 °C

4.1: 90 percent / ammonia / methanol / 14 h / 20 °C

With dmap; ammonium sulfate; ammonia; sodium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/00397910500213864

upstream raw materials:

3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose

Downstream raw materials:

(2'R,3'S,4'R)-1-(2',3'-di-benzyloxymethyl-tetrahydrofuran-4'-yl)-3-methoxycarbonyl-1,2,4-triazole

(2'R,3'S,4'R)-1-(2',3'-di-benzyloxymethyl-tetrahydrofuran-4'-yl)-3-aminocarbonyl-1,2,4-triazole

1,3-dideoxy-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-D-ribofuranose 2-(4-methylbenzenesulfonate)