(+)-(1S,2S,5S,6S,7R)-2-(hydroxymethyl)-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene

Base Information

• Chemical Name: (+)-(1S,2S,5S,6S,7R)-2-(hydroxymethyl)-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene
• CAS No.: 104816-21-9
• Molecular Formula: C₁₇H₂₀O₃
• Molecular Weight: 272.344

Synonyms:(+)-(1S,2S,5S,6S,7R)-2-(hydroxymethyl)-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene

Chemical Property of (+)-(1S,2S,5S,6S,7R)-2-(hydroxymethyl)-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene

Chemical Property:

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Technology Process of (+)-(1S,2S,5S,6S,7R)-2-(hydroxymethyl)-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene

There total 4 articles about (+)-(1S,2S,5S,6S,7R)-2-(hydroxymethyl)-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene 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: 91.0%

(+)-(1S,2S,5S,6S,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.02,6>dec-8-ene (104873-11-2) → (+)-(1S,2S,5S,6S,7R)-2-(hydroxymethyl)-5-(benzyloxy)-4-oxatricyclo<5.2.1.02,6>dec-8-ene (104816-21-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 23 ℃;

DOI:10.1016/S0040-4039(01)80899-6

Reference yield:

(-)-(2S)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde (104322-42-1) → (+)-(1S,2S,5S,6S,7R)-2-(hydroxymethyl)-5-(benzyloxy)-4-oxatricyclo<5.2.1.02,6>dec-8-ene (104816-21-9)

Guidance literature:

Multi-step reaction with 2 steps

2: 91 percent / NaBH₄ / ethanol / 23 °C

With sodium tetrahydroborate; In ethanol;

DOI:10.1016/S0040-4039(01)80899-6

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (+)-(1S,2S,5S,6S,7R)-2-(hydroxymethyl)-5-(benzyloxy)-4-oxatricyclo<5.2.1.02,6>dec-8-ene (104816-21-9)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 36 h / 50 °C / or at room temp. with tris(6,6,7,7,8,8,8-heptafluor-2,2-dimethyl-3,5-octanedione)europium(III) as catalyst

2: 65 percent / NaBH₄ / ethanol / 0.5 h / Ambient temperature

With sodium tetrahydroborate; In ethanol; toluene;

DOI:10.1021/jo00307a018

upstream raw materials:

(+)-(1S,2S,5S,6S,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene

(-)-(2S)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde

benzyl 2,3-anhydro-α-L-ribopyranoside

cyclopenta-1,3-diene

Downstream raw materials:

C₁₇H₂₀O₄

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