Benzoic acid (2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 284035-51-4
• Molecular Formula: C₂₆H₃₄O₆
• Molecular Weight: 442.552

Synonyms:Benzoic acid (2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

There total 5 articles about Benzoic acid (2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester 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: 58.0%

methanol (67-56-1) + 2-oxopropyl benzoate (6656-60-6) + (2S,3R)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanal (284035-47-8) → Benzoic acid (2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester (284035-51-4) + Benzoic acid (2R,4R,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

2-oxopropyl benzoate; (2S,3R)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanal; With di-n-butylboryl trifluoromethanesulfonate; In dichloromethane; at -78 - 0 ℃; for 3h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

methanol; With camphor-10-sulfonic acid; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(00)00383-X

Reference yield:

5-benzyloxy-1-pentanal (78999-24-3) → Benzoic acid (2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester (284035-51-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 78 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / 3 h / -78 - 0 °C

2.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

3.1: 74 percent / NaBH₄ / tetrahydrofuran; H₂O / 48 h / 20 °C

4.1: 97 percent / SO₃*Py; Et₃N / dimethylsulfoxide / 1 h / 20 °C

5.1: Bu₂BOTf / CH₂Cl₂ / 3 h / -78 - 0 °C

5.2: TBAF / tetrahydrofuran / 3 h / 20 °C

5.3: 58 percent / CSA / 1 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1.1: aldol coupling / 2.1: Etherification / 3.1: Reduction / 4.1: Oxidation / 5.1: aldol reaction / 5.2: deprotection / 5.3: ketalization;

DOI:10.1016/S0040-4039(00)00383-X

Reference yield:

(S)-4-Benzyl-3-((2S,3R)-7-benzyloxy-3-hydroxy-2-methyl-heptanoyl)-oxazolidin-2-one (171189-79-0) → Benzoic acid (2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester (284035-51-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2.1: 74 percent / NaBH₄ / tetrahydrofuran; H₂O / 48 h / 20 °C

3.1: 97 percent / SO₃*Py; Et₃N / dimethylsulfoxide / 1 h / 20 °C

4.1: Bu₂BOTf / CH₂Cl₂ / 3 h / -78 - 0 °C

4.2: TBAF / tetrahydrofuran / 3 h / 20 °C

4.3: 58 percent / CSA / 1 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1.1: Etherification / 2.1: Reduction / 3.1: Oxidation / 4.1: aldol reaction / 4.2: deprotection / 4.3: ketalization;

DOI:10.1016/S0040-4039(00)00383-X

upstream raw materials:

methanol

2-oxopropyl benzoate

(2S,3R)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanal

5-benzyloxy-1-pentanal

Downstream raw materials:

Benzoic acid (2R,4S,5S,6R)-6-(4-benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-carbaldehyde

[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methanol

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