[(2S)-3-[(2R,3R,4S,5S)-5-allyl-3-benzyloxy-4-hydroxytetrahydrofuran-2-yl]-2-benzoyloxypropyl]benzoate

Base Information

• Chemical Name: [(2S)-3-[(2R,3R,4S,5S)-5-allyl-3-benzyloxy-4-hydroxytetrahydrofuran-2-yl]-2-benzoyloxypropyl]benzoate
• CAS No.: 546141-24-6
• Molecular Formula: C₃₁H₃₂O₇
• Molecular Weight: 516.591

Synonyms:[(2S)-3-[(2R,3R,4S,5S)-5-allyl-3-benzyloxy-4-hydroxytetrahydrofuran-2-yl]-2-benzoyloxypropyl]benzoate

Chemical Property of [(2S)-3-[(2R,3R,4S,5S)-5-allyl-3-benzyloxy-4-hydroxytetrahydrofuran-2-yl]-2-benzoyloxypropyl]benzoate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of [(2S)-3-[(2R,3R,4S,5S)-5-allyl-3-benzyloxy-4-hydroxytetrahydrofuran-2-yl]-2-benzoyloxypropyl]benzoate

There total 12 articles about [(2S)-3-[(2R,3R,4S,5S)-5-allyl-3-benzyloxy-4-hydroxytetrahydrofuran-2-yl]-2-benzoyloxypropyl]benzoate 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: 71.0%

C31H32O8 (871348-02-6) + C31H32O8 (871348-03-7) + allyl-trimethyl-silane (762-72-1) → [(2S)-3-[(2R,3R,4S,5S)-5-allyl-3-benzyloxy-4-hydroxytetrahydrofuran-2-yl]-2-benzoyloxypropyl]benzoate (546141-24-6)

Guidance literature:

C₃₁H₃₂O₈; C₃₁H₃₂O₈; allyl-trimethyl-silane; With titanium(IV) isopropylate; titanium tetrachloride; In toluene; at 20 - 30 ℃; for 2h;

With hydrogenchloride; In water; toluene; at -5 - 30 ℃;

Reference yield:

[3-[(3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-benzoyloxypropyl] benzoate + allyl-trimethyl-silane (762-72-1) → [(2S)-3-[(2R,3R,4S,5S)-5-allyl-3-benzyloxy-4-hydroxytetrahydrofuran-2-yl]-2-benzoyloxypropyl]benzoate (546141-24-6)

Guidance literature:

With titanium(IV) isopropylate; titanium tetrachloride; In toluene; at 10 - 35 ℃;

Reference yield:

C31H32O8 (871348-03-7) + allyl-trimethyl-silane (762-72-1) → [(2S)-3-[(2R,3R,4S,5S)-5-allyl-3-benzyloxy-4-hydroxytetrahydrofuran-2-yl]-2-benzoyloxypropyl]benzoate (546141-24-6) + C31H32O6

Guidance literature:

With titanium(IV) isopropylate; titanium tetrachloride; In toluene; at 25 ℃; Overall yield = 100 %;

DOI:10.1055/s-0032-1317920

upstream raw materials:

C₃₁H₃₂O₈

C₃₁H₃₂O₈

allyl-trimethyl-silane

benzoyl chloride

Downstream raw materials:

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl) ethyl)-4-methylenetetrahydrofuran-2-yl)propyl pivalate

C₅₁H₉₀O₁₃S₂Si₂

2-((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)acetaldehyde

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