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

Base Information

• Chemical Name: (5-benzyloxy-6-benzyloxymethyl-2,2-dioxo-hexahydro-2λ⁶-benzo[1,3,2]dioxathiol-4-yloxy)-tert-butyl-dimethyl-silane
• CAS No.: 929038-76-6
• Molecular Formula: C₂₇H₃₈O₇SSi
• Molecular Weight: 534.746

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

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

Chemical Property:

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

There total 6 articles about (5-benzyloxy-6-benzyloxymethyl-2,2-dioxo-hexahydro-2λ⁶-benzo[1,3,2]dioxathiol-4-yloxy)-tert-butyl-dimethyl-silane 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: 88.0%

4-benzyloxy-5-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexane-1,2-diol (929038-75-5) → (5-benzyloxy-6-benzyloxymethyl-2,2-dioxo-hexahydro-2λ6-benzo[1,3,2]dioxathiol-4-yloxy)-tert-butyl-dimethyl-silane (929038-76-6)

Guidance literature:

4-benzyloxy-5-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexane-1,2-diol; With pyridine; ruthenium trichloride; thionyl chloride; In dichloromethane; at 0 ℃;

With sodium periodate; In tetrachloromethane; water; acetonitrile; at 20 ℃;

DOI:10.1246/cl.2007.36

Reference yield:

C26H40O4Si (929038-72-2) → (5-benzyloxy-6-benzyloxymethyl-2,2-dioxo-hexahydro-2λ6-benzo[1,3,2]dioxathiol-4-yloxy)-tert-butyl-dimethyl-silane (929038-76-6)

Guidance literature:

Multi-step reaction with 4 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

4.1: SOCl₂; RuCl₃*nH₂O; pyridine / CH₂Cl₂ / 0 °C

4.2: 88 percent / NaIO₄ / CCl₄; acetonitrile; H₂O / 20 °C

With pyridine; ruthenium trichloride; 9-borabicyclo[3.3.1]nonane dimer; thionyl chloride; 1-thiopropane; boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 4.1: Sharpless method;

DOI:10.1246/cl.2007.36

Reference yield:

C26H42O5Si (929038-73-3) → (5-benzyloxy-6-benzyloxymethyl-2,2-dioxo-hexahydro-2λ6-benzo[1,3,2]dioxathiol-4-yloxy)-tert-butyl-dimethyl-silane (929038-76-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / NaH / dimethylformamide / 0 °C

2.1: 87 percent / PrSH; BF₃*OEt₂ / -78 - -20 °C

3.1: SOCl₂; RuCl₃*nH₂O; pyridine / CH₂Cl₂ / 0 °C

3.2: 88 percent / NaIO₄ / CCl₄; acetonitrile; H₂O / 20 °C

With pyridine; ruthenium trichloride; thionyl chloride; 1-thiopropane; boron trifluoride diethyl etherate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; 3.1: Sharpless method;

DOI:10.1246/cl.2007.36

upstream raw materials:

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

C₂₆H₄₀O₄Si

C₂₆H₄₂O₅Si

C₃₃H₄₈O₅Si

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