(2R,3R,4R,4aS,10bR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8,9,10-trimethoxy-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene

Base Information

• Chemical Name: (2R,3R,4R,4aS,10bR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8,9,10-trimethoxy-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene
• CAS No.: 286425-51-2
• Molecular Formula: C₃₇H₄₀O₈
• Molecular Weight: 612.72
• Mol file: 286425-51-2.mol

Synonyms:(2R,3R,4R,4aS,10bR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8,9,10-trimethoxy-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene

Chemical Property of (2R,3R,4R,4aS,10bR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8,9,10-trimethoxy-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,4aS,10bR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8,9,10-trimethoxy-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene

There total 6 articles about (2R,3R,4R,4aS,10bR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8,9,10-trimethoxy-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene 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: 83.0%

(2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-5-(3,4,5-trimethoxy-benzyloxy)-tetrahydro-pyran (286425-50-1) → (2R,3R,4R,4aS,10bR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8,9,10-trimethoxy-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene (286425-51-2)

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/S0957-4166(99)00484-X

Reference yield:

4-Pentenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside (130781-26-9) → (2R,3R,4R,4aS,10bR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8,9,10-trimethoxy-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene (286425-51-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / NaH / dimethylformamide

2: 83 percent / iodonium dicollidine perchlorate / CH₂Cl₂ / 3 h / 20 °C

With iodonium di(2,4,6-trimethylpyridine) perchlorate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Cyclization;

DOI:10.1016/S0957-4166(99)00484-X

Reference yield:

1,2-O-(4-penten-1-yl)-orthoacetyl-3,4,6-tri-O-acetyl-α-D-glucopyranose (405282-85-1) → (2R,3R,4R,4aS,10bR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8,9,10-trimethoxy-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene (286425-51-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / KOH / tetrahydrofuran / Heating

2: trimethylsilyl triflate / CH₂Cl₂ / 2 h / 0 °C

3: MeONa; MeOH

4: 80 percent / NaH / dimethylformamide

5: 83 percent / iodonium dicollidine perchlorate / CH₂Cl₂ / 3 h / 20 °C

With methanol; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; iodonium di(2,4,6-trimethylpyridine) perchlorate; sodium methylate; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Benzylation / 2: Rearrangement / 3: Deacetylation / 4: Alkylation / 5: Cyclization;

DOI:10.1016/S0957-4166(99)00484-X

upstream raw materials:

(2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-5-(3,4,5-trimethoxy-benzyloxy)-tetrahydro-pyran

4-Pentenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside

1,2-O-(4-penten-1-yl)-orthoacetyl-3,4,6-tri-O-acetyl-α-D-glucopyranose

(3aR,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-methyl-2-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-b]pyran

Downstream raw materials:

(2R,3R,4R,4aS,10bS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8,9,10-trimethoxy-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene