ethyl(Z)-7-O-benzyl-6-O-(tetrahydropyranyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate

Base Information

• Chemical Name: ethyl(Z)-7-O-benzyl-6-O-(tetrahydropyranyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate
• CAS No.: 115828-21-2
• Molecular Formula: C₂₄H₃₂O₇
• Molecular Weight: 432.514

Synonyms:ethyl(Z)-7-O-benzyl-6-O-(tetrahydropyranyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate

Chemical Property of ethyl(Z)-7-O-benzyl-6-O-(tetrahydropyranyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate

Chemical Property:

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Technology Process of ethyl(Z)-7-O-benzyl-6-O-(tetrahydropyranyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate

There total 3 articles about ethyl(Z)-7-O-benzyl-6-O-(tetrahydropyranyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate 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:

3,4-dihydro-2H-pyran (110-87-2) + (Z)-ethyl-7-O-benzyl-4,5-O-isopropylidene-2,3-dideoxy-D-ribohept-2-enonate (99409-40-2) → ethyl(Z)-7-O-benzyl-6-O-(tetrahydropyranyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate (115828-21-2)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 0 - 25 ℃; for 1.5h;

DOI:10.1021/jo00263a017

Reference yield:

5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose (198969-39-0) → ethyl(Z)-7-O-benzyl-6-O-(tetrahydropyranyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate (115828-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / CH₂Cl₂ / 4 h / Heating

2: p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 1.5 h / 0 - 25 °C

With toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1021/jo00263a017

Reference yield:

5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose (198969-39-0) → (Z)-3-{(4S,5S)-5-[(R)-2-Benzyloxy-1-(tetrahydro-pyran-2-yloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester (115828-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂

2: 76 percent

In dichloromethane;

DOI:10.1016/S0040-4039(00)98347-3

upstream raw materials:

5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose

3,4-dihydro-2H-pyran

(Z)-ethyl-7-O-benzyl-4,5-O-isopropylidene-2,3-dideoxy-D-ribohept-2-enonate

Downstream raw materials:

(E)-3-{(4S,5S)-5-[(R)-2-Benzyloxy-1-(tetrahydro-pyran-2-yloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester

(E)-7-O-benzyl-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

((3aR,4R,6S,7S,7aR)-4-Benzyloxymethyl-7-iodo-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol

ethyl(E)-7-O-benzyl-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate

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