(R)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-1-[(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-butane-2,3-dione

Base Information

• Chemical Name: (R)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-1-[(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-butane-2,3-dione
• CAS No.: 909781-99-3
• Molecular Formula: C₅₄H₈₄O₁₀Si₃
• Molecular Weight: 977.511
• Mol file: 909781-99-3.mol

Synonyms:(R)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-1-[(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-butane-2,3-dione

Chemical Property of (R)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-1-[(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-butane-2,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-1-[(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-butane-2,3-dione

There total 4 articles about (R)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-1-[(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-butane-2,3-dione 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: 61.0%

(2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-6-{(S)-4-(tert-butyl-dimethyl-silanyloxy)-4-[(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-tetrahydro-pyran (911813-37-1) → (R)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-1-[(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-butane-2,3-dione (909781-99-3)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; In tetrachloromethane; water; acetonitrile;

DOI:10.1016/j.tetlet.2006.05.170

Reference yield:

((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane (909781-96-0) → (R)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-1-[(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-butane-2,3-dione (909781-99-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran / -80 °C

1.2: 73 percent / tetrahydrofuran / -80 - -20 °C

2.1: 86 percent / imidazole / dimethylformamide / 40 °C

3.1: 61 percent / RuO₂; NaIO₄ / CCl₄; acetonitrile; H₂O

With 1H-imidazole; ruthenium(IV) oxide; sodium periodate; n-butyllithium; In tetrahydrofuran; tetrachloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tetlet.2006.05.170

Reference yield:

(S)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-ol (909781-97-1) → (R)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-(tert-butyl-dimethyl-silanyloxy)-1-[(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-butane-2,3-dione (909781-99-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / imidazole / dimethylformamide / 40 °C

2: 61 percent / RuO₂; NaIO₄ / CCl₄; acetonitrile; H₂O

With 1H-imidazole; ruthenium(IV) oxide; sodium periodate; In tetrachloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tetlet.2006.05.170

upstream raw materials:

(2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-6-{(S)-4-(tert-butyl-dimethyl-silanyloxy)-4-[(2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-tetrahydro-pyran

((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

(S)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

(2'S,3'S)-3'-(tert-butyldimethylsiloxy)-tetrahydropyran-2'-carbaldehyde

Downstream raw materials:

(2R,3R,4S,4aS,5aS,6R,6aR,10aS,11aR,12aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-dodecahydro-1,5,7,11-tetraoxa-naphthacene-5a,6,11a-triol