(2R,3S,4S,5S,6R)-2-(2-Allyl-3,5,6-trimethoxy-4-methyl-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3S,4S,5S,6R)-2-(2-Allyl-3,5,6-trimethoxy-4-methyl-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran
• CAS No.: 717916-75-1
• Molecular Formula: C₃₇H₆₈O₆Si₂
• Molecular Weight: 665.114
• Mol file: 717916-75-1.mol

Synonyms:(2R,3S,4S,5S,6R)-2-(2-Allyl-3,5,6-trimethoxy-4-methyl-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran

Chemical Property of (2R,3S,4S,5S,6R)-2-(2-Allyl-3,5,6-trimethoxy-4-methyl-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5S,6R)-2-(2-Allyl-3,5,6-trimethoxy-4-methyl-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran

There total 18 articles about (2R,3S,4S,5S,6R)-2-(2-Allyl-3,5,6-trimethoxy-4-methyl-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran 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: 100.0%

methyl iodide (74-88-4) + 2-Allyl-3-{(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran-2-yl}-5-methoxy-6-methyl-benzene-1,4-diol (717916-74-0) → (2R,3S,4S,5S,6R)-2-(2-Allyl-3,5,6-trimethoxy-4-methyl-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran (717916-75-1)

Guidance literature:

With potassium carbonate; In acetone; Heating;

DOI:10.1039/b402391a

Reference yield:

3,5-dimethoxy-4-methylphenylmethyl alcohol (35052-27-8) → (2R,3S,4S,5S,6R)-2-(2-Allyl-3,5,6-trimethoxy-4-methyl-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran (717916-75-1)

Guidance literature:

Multi-step reaction with 17 steps

1.1: NaH / tetrahydrofuran / 0 °C

2.1: 82 percent / NaI; BF₃*OEt₂ / acetonitrile / 20 °C

3.1: NaHMDS / tetrahydrofuran / -78 °C

4.1: LiAlH₄ / tetrahydrofuran / -78 - 0 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

6.1: (R,R)-diisopropyl tartrate; 4 Angstroem molecular sieves / toluene / -78 °C

7.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

8.1: aq. OsO₄; NaIO₄ / tetrahydrofuran / 20 °C

9.1: n-BuLi / tetrahydrofuran / -78 °C

9.2: tetrahydrofuran

10.1: 100 percent / DMAP; pyridine / 20 °C

11.1: m-CPBA / CH₂Cl₂ / 20 °C

12.1: DIBAL-H / CH₂Cl₂ / -78 °C

13.1: 94 percent / Ag₂O / CH₂Cl₂ / 20 °C

14.1: (CF₃COO)2IPh; aq. K₂CO₃ / acetonitrile / 20 °C

14.2: 83 percent / aq. Na₂S₂O₄ / tetrahydrofuran / 0 °C

15.1: 100 percent / K₂CO₃ / acetone / Heating

16.1: 66 percent / N,N-dimethylaniline / 1.5 h / Heating

17.1: 100 percent / K₂CO₃ / acetone / Heating

With pyridine; 2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; L-(+)-diisopropyl tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; N,N-dimethyl-aniline; 3-chloro-benzenecarboperoxoic acid; bis-[(trifluoroacetoxy)iodo]benzene; sodium iodide; silver(l) oxide; In tetrahydrofuran; dichloromethane; acetone; toluene; acetonitrile; 16.1: Claisen rearrangement;

DOI:10.1039/b402391a

Reference yield:

methyl 3,5-dimethoxy-4-methylbenzoate (60441-79-4) → (2R,3S,4S,5S,6R)-2-(2-Allyl-3,5,6-trimethoxy-4-methyl-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran (717916-75-1)

Guidance literature:

Multi-step reaction with 18 steps

1.1: LiAlH₄ / tetrahydrofuran / 40 °C

2.1: NaH / tetrahydrofuran / 0 °C

3.1: 82 percent / NaI; BF₃*OEt₂ / acetonitrile / 20 °C

4.1: NaHMDS / tetrahydrofuran / -78 °C

5.1: LiAlH₄ / tetrahydrofuran / -78 - 0 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

7.1: (R,R)-diisopropyl tartrate; 4 Angstroem molecular sieves / toluene / -78 °C

8.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

9.1: aq. OsO₄; NaIO₄ / tetrahydrofuran / 20 °C

10.1: n-BuLi / tetrahydrofuran / -78 °C

10.2: tetrahydrofuran

11.1: 100 percent / DMAP; pyridine / 20 °C

12.1: m-CPBA / CH₂Cl₂ / 20 °C

13.1: DIBAL-H / CH₂Cl₂ / -78 °C

14.1: 94 percent / Ag₂O / CH₂Cl₂ / 20 °C

15.1: (CF₃COO)2IPh; aq. K₂CO₃ / acetonitrile / 20 °C

15.2: 83 percent / aq. Na₂S₂O₄ / tetrahydrofuran / 0 °C

16.1: 100 percent / K₂CO₃ / acetone / Heating

17.1: 66 percent / N,N-dimethylaniline / 1.5 h / Heating

18.1: 100 percent / K₂CO₃ / acetone / Heating

With pyridine; 2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; L-(+)-diisopropyl tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; N,N-dimethyl-aniline; 3-chloro-benzenecarboperoxoic acid; bis-[(trifluoroacetoxy)iodo]benzene; sodium iodide; silver(l) oxide; In tetrahydrofuran; dichloromethane; acetone; toluene; acetonitrile; 17.1: Claisen rearrangement;

DOI:10.1039/b402391a

upstream raw materials:

methyl iodide

2-Allyl-3-{(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran-2-yl}-5-methoxy-6-methyl-benzene-1,4-diol

3,5-dimethoxy-4-methylphenylmethyl alcohol

methyl 3,5-dimethoxy-4-methylbenzoate

Downstream raw materials:

(2-{(2R,3S,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran-2-yl}-3,4,6-trimethoxy-5-methyl-phenyl)-acetaldehyde