(2S,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-isopropoxy-2-vinyl-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2S,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-isopropoxy-2-vinyl-tetrahydro-pyran-3-ol
CAS No.:532401-51-7
Molecular Formula:C₂₄H₃₀O₅
Molecular Weight:398.499
Hs Code.:

Synonyms:(2S,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-isopropoxy-2-vinyl-tetrahydro-pyran-3-ol

Suppliers and Price of (2S,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-isopropoxy-2-vinyl-tetrahydro-pyran-3-ol

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Chemical Property of (2S,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-isopropoxy-2-vinyl-tetrahydro-pyran-3-ol

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Technology Process of (2S,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-isopropoxy-2-vinyl-tetrahydro-pyran-3-ol

There total 11 articles about (2S,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-isopropoxy-2-vinyl-tetrahydro-pyran-3-ol 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: 60.0%

: 67-63-0,8013-70-5
isopropyl alcohol

: 532401-40-4
(S)-1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-prop-2-en-1-ol

: 532401-44-8
(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-2-vinyl-tetrahydro-pyran-3-ol

: 532401-51-7
(2S,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-isopropoxy-2-vinyl-tetrahydro-pyran-3-ol

Guidance literature:: With camphor-10-sulfonic acid; at 120 ℃; for 48h;
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

: 532401-51-7
(2S,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-isopropoxy-2-vinyl-tetrahydro-pyran-3-ol

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: 35 percent / CSA / 48 h / 120 °C

With pyridine; dmap; oxalyl dichloride; camphor-10-sulfonic acid; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In 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

: 532401-51-7
(2S,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-isopropoxy-2-vinyl-tetrahydro-pyran-3-ol

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: 35 percent / CSA / 48 h / 120 °C

With pyridine; hydrogenchloride; dmap; oxalyl dichloride; camphor-10-sulfonic acid; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; 5: Swern oxidation;
DOI:10.1246/cl.2003.190