(3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

Base Information

• Chemical Name: (3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol
• CAS No.: 163039-18-7
• Molecular Formula: C₁₈H₂₄O₇
• Molecular Weight: 352.384
• Mol file: 163039-18-7.mol

Synonyms:(3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

Chemical Property of (3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

There total 5 articles about (3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 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: 95.0%

3,4,6-tri-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (123487-55-8) → (3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (163039-18-7)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; for 28h;

DOI:10.1021/ja00110a010

Reference yield:

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide (14218-11-2,14218-30-5,61198-88-7,108438-33-1,108836-02-8,114682-36-9,127305-34-4,151377-77-4) → (3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (163039-18-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-lutidine; Bu₄NI / CH₂Cl₂ / 24 h / Heating

2: 29.0 g / NaOMe / methanol; tetrahydrofuran

With 2,6-dimethylpyridine; sodium methylate; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4020(02)00671-3

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) → (3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (163039-18-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-lutidine; Bu₄NI / CH₂Cl₂ / 24 h / Heating

2: 29.0 g / NaOMe / methanol; tetrahydrofuran

With 2,6-dimethylpyridine; sodium methylate; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4020(02)00671-3

upstream raw materials:

3,4,6-tri-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide

n-Pent-4-enyl alcohol

1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside

Downstream raw materials:

3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)

(3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

2,3-di-O-acetyl-6-O-triphenylmethyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)

3,6-di-O-benzyl-4-O-p-methoxybenzyl-β-D-mannopyranose