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

Base Information

• Chemical Name: (2R,3R,4R,5R,6S)-3,4-Bis-benzyloxy-2-isopropoxy-5-methoxymethoxy-6-vinyl-tetrahydro-pyran
• CAS No.: 532401-45-9
• Molecular Formula: C₂₆H₃₄O₆
• Molecular Weight: 442.552
• Mol file: 532401-45-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (2R,3R,4R,5R,6S)-3,4-Bis-benzyloxy-2-isopropoxy-5-methoxymethoxy-6-vinyl-tetrahydro-pyran 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: 84.0%

chloromethyl methyl ether (107-30-2) + (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-2-vinyl-tetrahydro-pyran-3-ol (532401-44-8) → (2R,3R,4R,5R,6S)-3,4-Bis-benzyloxy-2-isopropoxy-5-methoxymethoxy-6-vinyl-tetrahydro-pyran (532401-45-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1246/cl.2003.190

Reference yield:

methyl ribofuranoside (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) → (2R,3R,4R,5R,6S)-3,4-Bis-benzyloxy-2-isopropoxy-5-methoxymethoxy-6-vinyl-tetrahydro-pyran (532401-45-9)

Guidance literature:

Multi-step reaction with 7 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: 60 percent / CSA / 48 h / 120 °C

6: 84 percent / NaH / tetrahydrofuran / 0 °C

With pyridine; dmap; oxalyl dichloride; camphor-10-sulfonic acid; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4: Swern oxidation;

DOI:10.1246/cl.2003.190

Reference yield:

D-Ribose (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) → (2R,3R,4R,5R,6S)-3,4-Bis-benzyloxy-2-isopropoxy-5-methoxymethoxy-6-vinyl-tetrahydro-pyran (532401-45-9)

Guidance literature:

Multi-step reaction with 8 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: 60 percent / CSA / 48 h / 120 °C

7: 84 percent / NaH / tetrahydrofuran / 0 °C

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

DOI:10.1246/cl.2003.190

upstream raw materials:

chloromethyl methyl ether

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

methyl ribofuranoside

D-Ribose

Downstream raw materials:

(R)-1-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-isopropoxy-3-methoxymethoxy-tetrahydro-pyran-2-yl)-ethane-1,2-diol