4-benzyloxy-5-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexane-1,2-diol

Base Information

• Chemical Name: 4-benzyloxy-5-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexane-1,2-diol
• CAS No.: 929038-75-5
• Molecular Formula: C₂₇H₄₀O₅Si
• Molecular Weight: 472.697

Synonyms:4-benzyloxy-5-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexane-1,2-diol

Chemical Property of 4-benzyloxy-5-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexane-1,2-diol

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Technology Process of 4-benzyloxy-5-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexane-1,2-diol

There total 5 articles about 4-benzyloxy-5-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexane-1,2-diol 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%

C33H48O5Si (929038-74-4) → 4-benzyloxy-5-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexane-1,2-diol (929038-75-5)

Guidance literature:

With 1-thiopropane; boron trifluoride diethyl etherate; at -78 - -20 ℃;

DOI:10.1246/cl.2007.36

Reference yield:

C26H40O4Si (929038-72-2) → 4-benzyloxy-5-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexane-1,2-diol (929038-75-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 9-BBN / tetrahydrofuran / Heating

1.2: 74 percent / aq. NaOH; H₂O₂ / 20 °C

2.1: 93 percent / NaH / dimethylformamide / 0 °C

3.1: 87 percent / PrSH; BF₃*OEt₂ / -78 - -20 °C

With 9-borabicyclo[3.3.1]nonane dimer; 1-thiopropane; boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1246/cl.2007.36

Reference yield:

C26H42O5Si (929038-73-3) → 4-benzyloxy-5-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexane-1,2-diol (929038-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / NaH / dimethylformamide / 0 °C

2: 87 percent / PrSH; BF₃*OEt₂ / -78 - -20 °C

With 1-thiopropane; boron trifluoride diethyl etherate; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1246/cl.2007.36

upstream raw materials:

C₃₃H₄₈O₅Si

C₂₆H₄₀O₄Si

C₂₆H₄₂O₅Si

(1R,2R,3S)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-methoxycarbonyl-4-cyclohexen-1,2,3-triol

Downstream raw materials:

(5-benzyloxy-6-benzyloxymethyl-2,2-dioxo-hexahydro-2λ⁶-benzo[1,3,2]dioxathiol-4-yloxy)-tert-butyl-dimethyl-silane

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