(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((1R,2R,3R,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((1R,2R,3R,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-3-ol
• CAS No.: 86461-99-6
• Molecular Formula: C₄₇H₅₀O₁₀
• Molecular Weight: 774.908
• Mol file: 86461-99-6.mol

Synonyms:

Chemical Property of (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((1R,2R,3R,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((1R,2R,3R,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-3-ol

There total 6 articles about (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((1R,2R,3R,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-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: 69.0%

O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose (113842-46-9) → (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((1R,2R,3R,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-3-ol (86461-99-6,113842-60-7)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 16h;

DOI:10.1016/0008-6215(87)80136-2

Reference yield: 2.8%

benzyl bromide (100-39-0) + 1,6-anhydro-2,2',3,3'-tetra-O-benzyl-β-lactose (86461-97-4) → O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose (86461-98-5) + O-(2,3,4-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose (73139-45-4) + 1,6-anhydro-2,2',3,3',6'-penta-O-benzyl-β-lactose (86461-99-6)

Guidance literature:

With barium dihydroxide; barium(II) oxide; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1248/cpb.31.75

Reference yield:

2,2',3,3'-tetra-O-acetyl-1,6-anhydro-4',6'-O-benzylidene-β-lactose (56889-23-7) → 1,6-anhydro-2,2',3,3',6'-penta-O-benzyl-β-lactose (86461-99-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 85.4 percent / powdered KOH / 3 h / 130 - 135 °C

2: 90.4 percent / 60percent aq. AcOH / ethanol; H₂O / 0.25 h / Heating

3: 34 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 2 h / Ambient temperature

With barium dihydroxide; potassium hydroxide; acetic acid; barium(II) oxide; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.31.75

upstream raw materials:

benzyl bromide

1,6-anhydro-2,2',3,3'-tetra-O-benzyl-β-lactose

1,6-anhydro-2,2',3,3'-tetra-O-benzyl-4',6'-O-benzylidene-β-lactose

2,2',3,3'-tetra-O-acetyl-1,6-anhydro-4',6'-O-benzylidene-β-lactose

Downstream raw materials:

1,6-anhydro-2,2',3,3',6'-penta-O-benzyl-4'-O-methyl-β-lactose

1,6-anhydromaltose