(S)-3-[(2R,3S,5R,6S)-3,5-Bis-benzyloxy-2-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde

Base Information

• Chemical Name: (S)-3-[(2R,3S,5R,6S)-3,5-Bis-benzyloxy-2-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde
• CAS No.: 126693-95-6
• Molecular Formula: C₂₇H₃₄O₅
• Molecular Weight: 438.564
• Mol file: 126693-95-6.mol

Synonyms:(S)-3-[(2R,3S,5R,6S)-3,5-Bis-benzyloxy-2-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde

Chemical Property of (S)-3-[(2R,3S,5R,6S)-3,5-Bis-benzyloxy-2-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(2R,3S,5R,6S)-3,5-Bis-benzyloxy-2-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde

There total 9 articles about (S)-3-[(2R,3S,5R,6S)-3,5-Bis-benzyloxy-2-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde 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:

1-[(2S,3R,5S,6R)-3,5-Bis-benzyloxy-6-((S)-3,4-dihydroxy-2-methyl-butyl)-6-methyl-tetrahydro-pyran-2-yl]-propan-2-one → (S)-3-[(2R,3S,5R,6S)-3,5-Bis-benzyloxy-2-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde (126693-95-6)

Guidance literature:

With sodium periodate; water; In tetrahydrofuran; at 25 ℃; for 2h; Yield given;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N

Reference yield:

(S)-1-((3aR,5S,6aR)-2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-methyl-pent-4-en-1-one (221372-53-8) → (S)-3-[(2R,3S,5R,6S)-3,5-Bis-benzyloxy-2-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde (126693-95-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / tetrahydrofuran; 1,2-dimethoxy-ethane / 1.) -78 deg C, 1 h, 2.) -30 deg C, 1.5 h; 25 deg C, 15 min

2: 92 percent / ZnCl₂ / CH₂Cl₂ / 1.5 h / 0 °C

3: 86 percent / NaH, n-Bu₄NI / tetrahydrofuran / 25 °C / 1.) 1 h, 2.) 11 h

4: 80 percent / N-chlorosuccinimide, 2,6-lutidine, H₂O / acetonitrile / 0.08 h / 0 °C

5: toluene / 4 h / 110 °C

6: NaH / tetrahydrofuran; paraffin / 10 h / 25 °C

7: N-methylmorpholine-N-oxide, OsO₄, H₂O / tetrahydrofuran / 5 h / 25 °C

8: NaIO₄, H₂O / tetrahydrofuran / 2 h / 25 °C

With 2,6-dimethylpyridine; sodium periodate; N-chloro-succinimide; osmium(VIII) oxide; water; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; zinc(II) chloride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; toluene; acetonitrile; paraffin;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N

Reference yield:

(S)-2-((3aR,5S,6aR)-2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hex-5-en-2-ol → (S)-3-[(2R,3S,5R,6S)-3,5-Bis-benzyloxy-2-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde (126693-95-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / ZnCl₂ / CH₂Cl₂ / 1.5 h / 0 °C

2: 86 percent / NaH, n-Bu₄NI / tetrahydrofuran / 25 °C / 1.) 1 h, 2.) 11 h

3: 80 percent / N-chlorosuccinimide, 2,6-lutidine, H₂O / acetonitrile / 0.08 h / 0 °C

4: toluene / 4 h / 110 °C

5: NaH / tetrahydrofuran; paraffin / 10 h / 25 °C

6: N-methylmorpholine-N-oxide, OsO₄, H₂O / tetrahydrofuran / 5 h / 25 °C

7: NaIO₄, H₂O / tetrahydrofuran / 2 h / 25 °C

With 2,6-dimethylpyridine; sodium periodate; N-chloro-succinimide; osmium(VIII) oxide; water; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; zinc(II) chloride; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; paraffin;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N

upstream raw materials:

(S)-1-((3aR,5S,6aR)-2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-methyl-pent-4-en-1-one

(2R,4S,5S,7S)-1,1-Bis-ethylsulfanyl-5,7-dimethyl-non-8-ene-2,4,5-triol

(R)-2-Benzenesulfonyl-1-((3aR,5S,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-methyl-pent-4-en-1-one

(3R,5S,6R)-3,5-Bis-benzyloxy-6-methyl-6-((S)-2-methyl-but-3-enyl)-tetrahydro-pyran-2-ol

Downstream raw materials:

Acetic acid (2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-3-acetoxy-2,11-bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yl ester

(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-10-(tert-butyl-diphenyl-silanyloxy)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-3-ol

(Z)-(4S,5aS,6aR,8R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-4,5,5a,6a,7,8,9,12a,13,13a-decahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene

(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-3,10-diol