1-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-propenone

Base Information

Chemical Name:1-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-propenone
CAS No.:532401-43-7
Molecular Formula:C₂₂H₂₄O₅
Molecular Weight:368.43
Hs Code.:

Synonyms:1-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-propenone

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Chemical Property of 1-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-propenone

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Technology Process of 1-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-propenone

There total 9 articles about 1-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-propenone 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: 98.0%

: 1826-67-1
vinyl magnesium bromide

: 532401-42-6
(2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-carboxylic acid methoxy-methyl-amide

: 532401-43-7
1-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-propenone

Guidance literature:: In tetrahydrofuran; at -78 ℃;
DOI:10.1246/cl.2003.190

Reference yield:

: 1824-96-0,1824-97-1,3795-68-4,3795-69-5,4229-54-3,5531-18-0,7473-45-2,13039-63-9,13039-64-0,13039-65-1,13039-67-3,22416-73-5,22861-09-2,25129-51-5,52485-92-4,52689-55-1,52689-56-2,56607-40-0,72880-70-7,79083-42-4,86782-30-1,86782-31-2,89615-03-2,89673-67-6,89707-99-3,102045-32-9,135910-17-7
methyl ribofuranoside

: 532401-43-7
1-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-propenone

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine; DMAP / 20 °C

2: 20 percent / NaH / dimethylformamide / 20 °C

3: 90 percent / p-TsOH*H₂O / methanol / 20 °C

4: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C

5: WSC; HOBt; iPr₂NEt / dimethylformamide / 20 °C

6: 98 percent / tetrahydrofuran / -78 °C

With pyridine; dmap; oxalyl dichloride; sodium hydride; benzotriazol-1-ol; toluene-4-sulfonic acid; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4: Swern oxidation;
DOI:10.1246/cl.2003.190

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-Ribose

: 532401-43-7
1-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-propenone

Guidance literature:: Multi-step reaction with 7 steps

1: HCl / 0 °C

2: pyridine; DMAP / 20 °C

3: 20 percent / NaH / dimethylformamide / 20 °C

4: 90 percent / p-TsOH*H₂O / methanol / 20 °C

5: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C

6: WSC; HOBt; iPr₂NEt / dimethylformamide / 20 °C

7: 98 percent / tetrahydrofuran / -78 °C

With pyridine; hydrogenchloride; dmap; oxalyl dichloride; sodium hydride; benzotriazol-1-ol; toluene-4-sulfonic acid; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5: Swern oxidation;
DOI:10.1246/cl.2003.190