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

Base Information

• Chemical Name: (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-{(S)-4-benzyloxy-4-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran
• CAS No.: 909782-11-2
• Molecular Formula: C₅₅H₇₆O₈Si₂
• Molecular Weight: 921.375

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

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

There total 3 articles about (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-{(S)-4-benzyloxy-4-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-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: 99.0%

(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) + benzyl bromide (100-39-0) → (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-{(S)-4-benzyloxy-4-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran (909782-11-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

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-6-{(S)-4-benzyloxy-4-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran (909782-11-2)

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: 99 percent / NaH / tetrahydrofuran; dimethylformamide

With n-butyllithium; sodium hydride; 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-6-{(S)-4-benzyloxy-4-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-2-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran (909782-11-2)

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: 99 percent / NaH / tetrahydrofuran; dimethylformamide

With n-butyllithium; sodium hydride; 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

benzyl bromide

((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,6aS,10aS,11aR,12aS)-3,4,6-Tris-benzyloxy-2-benzyloxymethyl-dodecahydro-1,5,7,11-tetraoxa-naphthacene-5a,11a-diol

(R)-1-Benzyloxy-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]-butane-2,3-dione

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