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

Base Information

• Chemical Name: (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-methyl-2-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-b]pyran
• CAS No.: 128503-36-6
• Molecular Formula: C₃₄H₄₀O₇
• Molecular Weight: 560.687

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

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

Chemical Property:

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

There total 2 articles about (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-methyl-2-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-b]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: 92.0%

benzyl bromide (100-39-0) + 1,2-O-(4-penten-1-yl)-orthoacetyl-3,4,6-tri-O-acetyl-α-D-mannopyranose (647832-29-9) → (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-methyl-2-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-b]pyran (128503-36-6)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; Heating;

DOI:10.1016/j.tetlet.2003.10.006

Reference yield:

acetobromomannose (13242-53-0) → (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-methyl-2-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-b]pyran (128503-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / nBu₄NBr / 2,4,6-trimethyl-pyridine

2: 92 percent / KOH / tetrahydrofuran / Heating

With potassium hydroxide; tetrabutylammomium bromide; In tetrahydrofuran; 2,4,6-trimethyl-pyridine;

DOI:10.1016/j.tetlet.2003.10.006

Reference yield: 73.0%

(3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-methyl-2-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-b]pyran (128503-36-6) + C32H32O9 (128503-37-7) → C61H62O15

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane;

DOI:10.1039/c39900000270

upstream raw materials:

benzyl bromide

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

acetobromomannose

Downstream raw materials:

4-penten-1-yl 2-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranoside

pent-4-enyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside

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

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

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