(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

Base Information

• Chemical Name: (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
• CAS No.: 911813-37-1
• Molecular Formula: C₅₄H₈₄O₈Si₃
• Molecular Weight: 945.513

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 3 articles about (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 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: 86.0%

(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) + tert-butyldimethylsilyl chloride (18162-48-6) → (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)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 40 ℃;

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) → (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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2006.05.170

Reference yield:

(2'S,3'S)-3'-(tert-butyldimethylsiloxy)-tetrahydropyran-2'-carbaldehyde (125877-83-0) → (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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2006.05.170

upstream raw materials:

(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

tert-butyldimethylsilyl chloride

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

(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

(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

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