(2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran

Base Information

• Chemical Name: (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran
• CAS No.: 895140-72-4
• Molecular Formula: C₇₄H₇₈O₁₃
• Molecular Weight: 1175.43
• Mol file: 895140-72-4.mol

Synonyms:(2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran

Chemical Property of (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran

There total 8 articles about (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-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: 81.0%

benzyl bromide (100-39-0) + (3aS,4R,6S,7R,7aS)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-4-triisopropylsilanyloxymethyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one (162128-74-7) → (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran (895140-72-4)

Guidance literature:

(3aS,4R,6S,7R,7aS)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-4-triisopropylsilanyloxymethyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one; With tetrabutyl ammonium fluoride; In tetrahydrofuran;

benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20010504)40:9<1728::AID-ANIE17280>3.0.CO;2-1

Reference yield:

2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride (127061-08-9) → (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran (895140-72-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: SnCl₂; AgOTf; di-tert-butylpyridine

2.1: TBAF / tetrahydrofuran / 2 h / 20 °C

3.1: K₂CO₃ / methanol / 12 h / 20 °C

4.1: NaH / dimethylformamide / 0.5 h / 0 °C

4.2: 9.05 g / dimethylformamide / 14 h / 20 °C

With tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; sodium hydride; potassium carbonate; Di-tert-butylpyridine; tin(ll) chloride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.02.080

Reference yield:

3,6-di-O-benzyl-D-glucal (145852-76-2) → (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran (895140-72-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DMDO / CH₂Cl₂

1.2: ZnCl₂

1.3: 50 percent / SnCl₂; AgOTf; DTBP / CH₂Cl₂

2.1: TBAF / tetrahydrofuran

2.2: 81 percent / NaH / dimethylformamide

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/1521-3773(20010504)40:9<1728::AID-ANIE17280>3.0.CO;2-1

upstream raw materials:

benzyl bromide

(3aS,4R,6S,7R,7aS)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-4-triisopropylsilanyloxymethyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride

(3aS,4R,6S,7R,7aS)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-4-hydroxymethyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

Downstream raw materials:

2-trimethylsilanyl-ethanesulfonic acid {4-benzyloxy-6-benzyloxymethyl-5-[4,5-bis-benzyloxy-6-benzyloxymethyl-3-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-ethylsulfanyl-tetrahydro-pyran-3-yl}-amide