(1S,3S,4S,5R,6R,8S)-4,5-Bis-benzyloxy-1-methyl-2,7,9,10-tetraoxa-tricyclo[4.3.2.0^3,8]undecane

Base Information

• Chemical Name: (1S,3S,4S,5R,6R,8S)-4,5-Bis-benzyloxy-1-methyl-2,7,9,10-tetraoxa-tricyclo[4.3.2.0^3,8]undecane
• CAS No.: 246852-75-5
• Molecular Formula: C₂₂H₂₄O₆
• Molecular Weight: 384.429

Synonyms:(1S,3S,4S,5R,6R,8S)-4,5-Bis-benzyloxy-1-methyl-2,7,9,10-tetraoxa-tricyclo[4.3.2.0^3,8]undecane

Chemical Property of (1S,3S,4S,5R,6R,8S)-4,5-Bis-benzyloxy-1-methyl-2,7,9,10-tetraoxa-tricyclo[4.3.2.0^3,8]undecane

Chemical Property:

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Technology Process of (1S,3S,4S,5R,6R,8S)-4,5-Bis-benzyloxy-1-methyl-2,7,9,10-tetraoxa-tricyclo[4.3.2.0^3,8]undecane

There total 3 articles about (1S,3S,4S,5R,6R,8S)-4,5-Bis-benzyloxy-1-methyl-2,7,9,10-tetraoxa-tricyclo[4.3.2.0^3,8]undecane 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:

1,2-O-(Allyloxyethyliden)-β-D-mannopyranose (136944-92-8) → (1S,3S,4S,5R,6R,8S)-4,5-Bis-benzyloxy-1-methyl-2,7,9,10-tetraoxa-tricyclo[4.3.2.03,8]undecane (246852-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium trifluoromethanesulfonate / pyridine / 8 h / 20 °C

2: NaH / dimethylformamide

With pyridinium triflate; sodium hydride; In pyridine; N,N-dimethyl-formamide; 1: Cyclization / 2: Etherification;

DOI:10.1016/S0040-4039(99)01193-4

Reference yield:

1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (29073-91-4,55865-04-8,138196-19-7) → (1S,3S,4S,5R,6R,8S)-4,5-Bis-benzyloxy-1-methyl-2,7,9,10-tetraoxa-tricyclo[4.3.2.03,8]undecane (246852-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole*HCl / dimethylformamide / 8 h / 20 °C

2: NaH / dimethylformamide

With Imidazole hydrochloride; sodium hydride; In N,N-dimethyl-formamide; 1: Cyclization / 2: Etherification;

DOI:10.1016/S0040-4039(99)01193-4

Reference yield:

benzyl chloride (100-44-7) + (1S,3S,4S,5S,6R,8S)-1-Methyl-2,7,9,10-tetraoxa-tricyclo[4.3.2.03,8]undecane-4,5-diol → (1S,3S,4S,5R,6R,8S)-4,5-Bis-benzyloxy-1-methyl-2,7,9,10-tetraoxa-tricyclo[4.3.2.03,8]undecane (246852-75-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(99)01193-4

upstream raw materials:

benzyl chloride

1,2-O-(Allyloxyethyliden)-β-D-mannopyranose

1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

Downstream raw materials:

2-O-Acetyl-1,6-anhydro-3,4-di-O-benzyl-β-D-mannopyranose

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