3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose

Base Information

Chemical Name:3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose
CAS No.:229469-36-7
Molecular Formula:C₁₇H₂₆O₁₀S₂
Molecular Weight:454.519
Hs Code.:

Synonyms:3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose

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Chemical Property of 3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose

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Technology Process of 3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose

There total 20 articles about 3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose 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: 90.0%

: Methanesulfonic acid (3S,4R,5S)-3-benzyloxy-2-methanesulfonyloxymethyl-5-methoxy-4-trityloxymethyl-tetrahydro-furan-2-ylmethyl ester

: 229469-36-7
3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose

Guidance literature:: With acetic acid; In water; at 20 ℃; for 2h;
DOI:10.1080/15257779908041488

Reference yield:

: 56607-40-0
methyl D-arabinofuranoside

: 229469-36-7
3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose

Guidance literature:: Multi-step reaction with 13 steps

1.1: 71 percent / DMAP / pyridine / 12 h / 20 °C

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

3.1: 56 percent / diethyl ether / 1 h / -10 °C

4.1: 100 percent / TBAF / tetrahydrofuran / 48 h / 20 °C

5.1: pyridine

6.1: 71 percent / NaH / tetrahydrofuran / 5 h / 20 °C

7.1: 9-BBN / tetrahydrofuran / 14 h / 40 °C

7.2: 93 percent / NaBO₃ / H₂O / 4 h / 50 °C

8.1: pyridine / 16 h / 20 °C

9.1: 94 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

10.1: 90 percent / DCC, TFA, DMSO / pyridine / 6 h / 20 °C

11.1: 95 percent / NaOH / H₂O; dioxane / 48 h / 20 °C

12.1: pyridine / 0.25 h / 20 °C

13.1: 90 percent / AcOH / H₂O / 2 h / 20 °C

With dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; water; 1.1: Substitution / 2.1: Oxidation / 3.1: Wittig reaction / 4.1: desilylation / 5.1: Substitution / 6.1: Substitution / 7.1: Addition / 7.2: Reduction / 8.1: Substitution / 9.1: Substitution / 10.1: Oxidation / 11.1: Addition / 12.1: Esterification / 13.1: Hydrolysis;
DOI:10.1080/15257779908041488

Reference yield:

: 229469-30-1
(2R,3S,5S)-2-Hydroxymethyl-5-methoxy-4-methylene-tetrahydro-furan-3-ol

: 229469-36-7
3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose

Guidance literature:: Multi-step reaction with 9 steps

1.1: pyridine

2.1: 71 percent / NaH / tetrahydrofuran / 5 h / 20 °C

3.1: 9-BBN / tetrahydrofuran / 14 h / 40 °C

3.2: 93 percent / NaBO₃ / H₂O / 4 h / 50 °C

4.1: pyridine / 16 h / 20 °C

5.1: 94 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

6.1: 90 percent / DCC, TFA, DMSO / pyridine / 6 h / 20 °C

7.1: 95 percent / NaOH / H₂O; dioxane / 48 h / 20 °C

8.1: pyridine / 0.25 h / 20 °C

9.1: 90 percent / AcOH / H₂O / 2 h / 20 °C

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; water; 1.1: Substitution / 2.1: Substitution / 3.1: Addition / 3.2: Reduction / 4.1: Substitution / 5.1: Substitution / 6.1: Oxidation / 7.1: Addition / 8.1: Esterification / 9.1: Hydrolysis;
DOI:10.1080/15257779908041488