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

Base Information

• Chemical Name: 1,2-O-(4-penten-1-yl)-orthoacetyl-3,4,6-tri-O-acetyl-α-D-glucopyranose
• CAS No.: 405282-85-1
• Molecular Formula: C₁₉H₂₈O₁₀
• Molecular Weight: 416.425
• Mol file: 405282-85-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 1,2-O-(4-penten-1-yl)-orthoacetyl-3,4,6-tri-O-acetyl-α-D-glucopyranose 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: 31.0%

n-Pent-4-enyl alcohol (821-09-0) + 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate (1219934-69-6) → 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-D-glucopyranose (55864-99-8) + 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) + n-pent-4-enyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside + n-pent-4-enyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside (1126092-75-8) + n-pent-4-enyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (50256-33-2) + 1,2-O-(4-penten-1-yl)-orthoacetyl-3,4,6-tri-O-acetyl-α-D-glucopyranose (405282-85-1)

Guidance literature:

With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); In dichloromethane; at 20 ℃; for 3h; optical yield given as %de; Molecular sieve;

DOI:10.1039/c1cc11680k

Reference yield: 84.0%

benzyl bromide (100-39-0) + 1,2-O-(4-penten-1-yl)-orthoacetyl-3,4,6-tri-O-acetyl-α-D-glucopyranose (405282-85-1) → (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 (405283-35-4)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; Heating;

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) → 4-Pentenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside (130781-26-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / KOH / tetrahydrofuran / Heating

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

3: MeONa; MeOH

With methanol; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In tetrahydrofuran; dichloromethane; 1: Benzylation / 2: Rearrangement / 3: Deacetylation;

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

upstream raw materials:

n-Pent-4-enyl alcohol

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate

Downstream raw materials:

(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

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

(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

(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