2-benzyloxy-3-deoxy-6,7-O-isopropylidene-D-arabinohept-2-enoic-γ-lactone

Base Information

• Chemical Name: 2-benzyloxy-3-deoxy-6,7-O-isopropylidene-D-arabinohept-2-enoic-γ-lactone
• CAS No.: 868566-23-8
• Molecular Formula: C₁₇H₂₀O₆
• Molecular Weight: 320.342

Synonyms:2-benzyloxy-3-deoxy-6,7-O-isopropylidene-D-arabinohept-2-enoic-γ-lactone

Chemical Property of 2-benzyloxy-3-deoxy-6,7-O-isopropylidene-D-arabinohept-2-enoic-γ-lactone

Chemical Property:

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Technology Process of 2-benzyloxy-3-deoxy-6,7-O-isopropylidene-D-arabinohept-2-enoic-γ-lactone

There total 3 articles about 2-benzyloxy-3-deoxy-6,7-O-isopropylidene-D-arabinohept-2-enoic-γ-lactone 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: 81.0%

2-O-benzyl-3,5;6,7-di-O-isopropylidene-D-glucoheptonic-γ-lactone (868566-24-9) → 2-benzyloxy-3-deoxy-6,7-O-isopropylidene-D-arabinohept-2-enoic-γ-lactone (868566-23-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 0.25h;

DOI:10.1021/jo050972v

Reference yield:

3,5:6,7-bis-O-(1-methylethylidene)-α-D-glucoheptonic γ-lactone (6605-22-7) → 2-benzyloxy-3-deoxy-6,7-O-isopropylidene-D-arabinohept-2-enoic-γ-lactone (868566-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Ag₂O / CH₂Cl₂ / 6 h / Heating

2: 81 percent / t-BuOK / tetrahydrofuran / 0.25 h / -78 °C

With potassium tert-butylate; silver(l) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo050972v

Reference yield:

benzyl bromide (100-39-0) → 2-benzyloxy-3-deoxy-6,7-O-isopropylidene-D-arabinohept-2-enoic-γ-lactone (868566-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Ag₂O / CH₂Cl₂ / 6 h / Heating

2: 81 percent / t-BuOK / tetrahydrofuran / 0.25 h / -78 °C

With potassium tert-butylate; silver(l) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo050972v

upstream raw materials:

2-O-benzyl-3,5;6,7-di-O-isopropylidene-D-glucoheptonic-γ-lactone

3,5:6,7-bis-O-(1-methylethylidene)-α-D-glucoheptonic γ-lactone

benzyl bromide

Downstream raw materials:

(5R,7R,9S)-5-Hydroxy-7,9-bis-(4-methoxy-benzyloxy)-13-phenyl-tridec-2-ynoic acid methyl ester

(Z)-(5R,7R,9S)-5-Hydroxy-7,9-bis-(4-methoxy-benzyloxy)-13-phenyl-tridec-2-enoic acid methyl ester

(R)-6-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-5,6-dihydro-pyran-2-one

(2S,4R,6S)-4,6-Bis-(4-methoxy-benzyloxy)-10-phenyl-decane-1,2-diol

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