(R)-2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethanol

Base Information

• Chemical Name: (R)-2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethanol
• CAS No.: 328046-73-7
• Molecular Formula: C₄₈H₅₄O₁₀
• Molecular Weight: 790.951
• Mol file: 328046-73-7.mol

Synonyms:(R)-2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethanol

Chemical Property of (R)-2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethanol

There total 10 articles about (R)-2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethanol 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: 92.0%

ethyl 5-O-(2',3',5'-tri-O-benzyl-α-D-arabinofuranosyl)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactofuranoside (328046-72-6) → (R)-2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethanol (328046-73-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/ol0002976

Reference yield:

1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9,43225-70-3) → (R)-2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethanol (328046-73-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / n-Bu₃SnOEt / 1,2-dichloro-ethane / 3 h / Heating

2: 65 percent / DBU / CH₂Cl₂ / 2 h / 0 °C

3: 4 Angstyroem molecular sieves; BF₃*OEt₂ / CH₂Cl₂ / 2 h / 20 °C

4: 2.03 g / NaOMe / methanol / 2 h / 20 °C

5: 87 percent / NaH / dimethylformamide / 3 h / 20 °C

6: 92 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; tributyltin ethoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo010180a

Reference yield:

Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-tetrahydro-furan-3-yl ester (328046-70-4) → (R)-2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethanol (328046-73-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.03 g / NaOMe / methanol / 2 h / 20 °C

2: 87 percent / NaH / dimethylformamide / 3 h / 20 °C

3: 92 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

With tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo010180a

upstream raw materials:

ethyl 5-O-(2',3',5'-tri-O-benzyl-α-D-arabinofuranosyl)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactofuranoside

1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose

benzyl bromide

ethyl 2,3-di-O-benzyl-β-D-galactofuranoside

Downstream raw materials:

ethyl 5-O-(2',3',5'-tri-O-benzyl-α-D-arabinofuranosyl)-6-O-(β-D-galactofuranosyl)-2,3-di-O-benzyl-β-D-galactofuranoside

acetic acid 4-acetoxy-2-[2-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-(3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethoxy]-5-(1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester