1,2-O-(1-methylethylidene)-3-deoxy-3-(hydroxymethyl)-5-O-benzyl-L-ribofuranose

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Chemical Name:1,2-O-(1-methylethylidene)-3-deoxy-3-(hydroxymethyl)-5-O-benzyl-L-ribofuranose
CAS No.:268750-14-7
Molecular Formula:C₁₆H₂₂O₅
Molecular Weight:294.348
Hs Code.:

Synonyms:1,2-O-(1-methylethylidene)-3-deoxy-3-(hydroxymethyl)-5-O-benzyl-L-ribofuranose

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Chemical Property of 1,2-O-(1-methylethylidene)-3-deoxy-3-(hydroxymethyl)-5-O-benzyl-L-ribofuranose

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Technology Process of 1,2-O-(1-methylethylidene)-3-deoxy-3-(hydroxymethyl)-5-O-benzyl-L-ribofuranose

There total 6 articles about 1,2-O-(1-methylethylidene)-3-deoxy-3-(hydroxymethyl)-5-O-benzyl-L-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: 79.0%

: 268750-13-6
1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose

: 268750-14-7
1,2-O-(1-methylethylidene)-3-deoxy-3-(hydroxymethyl)-5-O-benzyl-L-ribofuranose

Guidance literature:: 1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; for 3h; cooling;
DOI:10.1080/15257770008033005

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
L-xylopyranose

: 268750-14-7
1,2-O-(1-methylethylidene)-3-deoxy-3-(hydroxymethyl)-5-O-benzyl-L-ribofuranose

Guidance literature:: Multi-step reaction with 6 steps

1.1: CuSO₄; H₂SO₄ / acetone / 36 h / 20 °C

1.2: 98 percent / aq. HCl / H₂O / 6 h

2.1: 71 percent / pyridine / CHCl₃ / 20 °C

3.1: 85 percent / 17 h / 100 °C

4.1: 99 percent / dess-Martin periodinane / CH₂Cl₂ / 3.5 h / 20 °C

5.1: phenyl lithium / tetrahydrofuran / 1 h / -78 °C

5.2: 71 percent / tetrahydrofuran / -78 - 55 °C

6.1: BH₃-Me₂S / tetrahydrofuran / 1 h / 0 - 20 °C

6.2: 79 percent / H₂O₂; NaOH / H₂O; tetrahydrofuran / 3 h / cooling

With pyridine; dimethylsulfide borane complex; sulfuric acid; Dess-Martin periodane; copper(II) sulfate; phenyllithium; In tetrahydrofuran; dichloromethane; chloroform; acetone; 1.1: Condensation / 1.2: Hydrolysis / 2.1: Tosylation / 3.1: Substitution / 4.1: Dess-Martin oxidation / 5.1: deprotonation / 5.2: Wittig reaction / 6.1: hydroboration / 6.2: Hydrolysis;
DOI:10.1080/15257770008033005

Reference yield:

: 114861-22-2
1,2-O-isopropylidene-α-L-xylofuranose

: 268750-14-7
1,2-O-(1-methylethylidene)-3-deoxy-3-(hydroxymethyl)-5-O-benzyl-L-ribofuranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: 71 percent / pyridine / CHCl₃ / 20 °C

2.1: 85 percent / 17 h / 100 °C

3.1: 99 percent / dess-Martin periodinane / CH₂Cl₂ / 3.5 h / 20 °C

4.1: phenyl lithium / tetrahydrofuran / 1 h / -78 °C

4.2: 71 percent / tetrahydrofuran / -78 - 55 °C

5.1: BH₃-Me₂S / tetrahydrofuran / 1 h / 0 - 20 °C

5.2: 79 percent / H₂O₂; NaOH / H₂O; tetrahydrofuran / 3 h / cooling

With pyridine; dimethylsulfide borane complex; Dess-Martin periodane; phenyllithium; In tetrahydrofuran; dichloromethane; chloroform; 1.1: Tosylation / 2.1: Substitution / 3.1: Dess-Martin oxidation / 4.1: deprotonation / 4.2: Wittig reaction / 5.1: hydroboration / 5.2: Hydrolysis;
DOI:10.1080/15257770008033005