(S)-5-{(2R,3S,5R,6S)-3,5-Bis-benzyloxy-6-[3-benzyloxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-methyl-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid benzyl ester

Base Information

• Chemical Name: (S)-5-{(2R,3S,5R,6S)-3,5-Bis-benzyloxy-6-[3-benzyloxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-methyl-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid benzyl ester
• CAS No.: 221464-83-1
• Molecular Formula: C₅₇H₈₂O₉Si₂
• Molecular Weight: 967.444
• Mol file: 221464-83-1.mol

Synonyms:(S)-5-{(2R,3S,5R,6S)-3,5-Bis-benzyloxy-6-[3-benzyloxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-methyl-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid benzyl ester

Chemical Property of (S)-5-{(2R,3S,5R,6S)-3,5-Bis-benzyloxy-6-[3-benzyloxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-methyl-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-{(2R,3S,5R,6S)-3,5-Bis-benzyloxy-6-[3-benzyloxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-methyl-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid benzyl ester

There total 10 articles about (S)-5-{(2R,3S,5R,6S)-3,5-Bis-benzyloxy-6-[3-benzyloxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-methyl-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid benzyl 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: 81.0%

(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) + 1-<(tert-butyldimethylsilyl)oxy>-1-(benzyloxy)ethylene (92144-04-2) → (S)-5-{(2R,3S,5R,6S)-3,5-Bis-benzyloxy-6-[3-benzyloxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-methyl-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid benzyl ester (221464-83-1)

Guidance literature:

With zinc dibromide; In diethyl ether; at -78 ℃; for 0.5h;

DOI:10.1021/ja00165a085

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)-5-{(2R,3S,5R,6S)-3,5-Bis-benzyloxy-6-[3-benzyloxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-methyl-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid benzyl ester (221464-83-1)

Guidance literature:

Multi-step reaction with 9 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

9: 81 percent / ZnBr₂ / diethyl ether / 0.33 h / -78 °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; zinc dibromide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; 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)-5-{(2R,3S,5R,6S)-3,5-Bis-benzyloxy-6-[3-benzyloxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-methyl-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid benzyl ester (221464-83-1)

Guidance literature:

Multi-step reaction with 8 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

8: 81 percent / ZnBr₂ / diethyl ether / 0.33 h / -78 °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; zinc dibromide; In tetrahydrofuran; diethyl ether; 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)-3-[(2R,3S,5R,6S)-3,5-Bis-benzyloxy-2-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde

1-<(tert-butyldimethylsilyl)oxy>-1-(benzyloxy)ethylene

(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

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