(S)-1-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-(tert-butyl-dimethyl-silanyl)-prop-2-yn-1-ol

Base Information

• Chemical Name: (S)-1-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-(tert-butyl-dimethyl-silanyl)-prop-2-yn-1-ol
• CAS No.: 162189-47-1
• Molecular Formula: C₂₄H₃₈O₄Si
• Molecular Weight: 418.649
• Mol file: 162189-47-1.mol

Synonyms:(S)-1-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-(tert-butyl-dimethyl-silanyl)-prop-2-yn-1-ol

Chemical Property of (S)-1-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-(tert-butyl-dimethyl-silanyl)-prop-2-yn-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-(tert-butyl-dimethyl-silanyl)-prop-2-yn-1-ol

There total 10 articles about (S)-1-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-(tert-butyl-dimethyl-silanyl)-prop-2-yn-1-ol 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: 87.0%

(tert-butyldimethylsilyl)acetylene (86318-61-8) + methyl 6-aldehydo-3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-14-0) → (S)-1-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-(tert-butyl-dimethyl-silanyl)-prop-2-yn-1-ol (162189-47-1)

Guidance literature:

With methyllithium; magnesium bromide; at -30 ℃; for 0.5h;

Reference yield:

Methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside (101978-79-4) → (S)-1-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-(tert-butyl-dimethyl-silanyl)-prop-2-yn-1-ol (162189-47-1)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / 10percent Pd/C / ethyl acetate; ethanol / 1 h / Ambient temperature

2: DMAP, NEt₃ / CH₂Cl₂ / 2 h / Ambient temperature

3: 82 percent / Et₃N / 1,2-dichloro-ethane / 0.5 h / 100 °C

4: 1.) TMEDA, 2.) MeLi / 1.) THF, 10 min, 2.) THF, Et₂O, -78 deg C, 45 min; reflux, 4 h

5: 94 percent / CuBr / tetrahydrofuran; diethyl ether / 0.75 h / Ambient temperature

6: 89 percent / NaH, Bu₄NI / tetrahydrofuran / 6 h / Ambient temperature

7: 87 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

8: 1.) (COCl)2, DMSO, 2.) NEt₃ / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂

9: 1.) MeLi, Li / 1.) THF, -78 deg C, 2.) THF, -30 deg C

With dmap; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; methyllithium; hydrogen; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; dimethyl sulfoxide; triethylamine; copper(I) bromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane;

DOI:10.1055/s-1999-3671

Reference yield:

methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside (194149-26-3) → (S)-1-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-(tert-butyl-dimethyl-silanyl)-prop-2-yn-1-ol (162189-47-1)

Guidance literature:

Multi-step reaction with 10 steps

2: H₂ / 10percent Pd/C / ethyl acetate; ethanol / 1 h / Ambient temperature

3: DMAP, NEt₃ / CH₂Cl₂ / 2 h / Ambient temperature

4: 82 percent / Et₃N / 1,2-dichloro-ethane / 0.5 h / 100 °C

5: 1.) TMEDA, 2.) MeLi / 1.) THF, 10 min, 2.) THF, Et₂O, -78 deg C, 45 min; reflux, 4 h

6: 94 percent / CuBr / tetrahydrofuran; diethyl ether / 0.75 h / Ambient temperature

7: 89 percent / NaH, Bu₄NI / tetrahydrofuran / 6 h / Ambient temperature

8: 87 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

9: 1.) (COCl)2, DMSO, 2.) NEt₃ / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂

10: 1.) MeLi, Li / 1.) THF, -78 deg C, 2.) THF, -30 deg C

With dmap; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; methyllithium; hydrogen; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; dimethyl sulfoxide; triethylamine; copper(I) bromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane;

DOI:10.1055/s-1999-3671

upstream raw materials:

(tert-butyldimethylsilyl)acetylene

methyl 6-aldehydo-3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside

Methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside

methyl 3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside

Downstream raw materials:

(4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane

{(S)-3-[(4S,5R,6R)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-3-methoxy-prop-1-ynyl}-tert-butyl-dimethyl-silane

tert-Butyl-{(S)-3-methoxy-3-[(4S,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-prop-1-ynyl}-dimethyl-silane

[(S)-3-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-methoxy-prop-1-ynyl]-tert-butyl-dimethyl-silane