tert-Butyl-dimethyl-{4-[(3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-benzyloxy}-silane

Base Information

• Chemical Name: tert-Butyl-dimethyl-{4-[(3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-benzyloxy}-silane
• CAS No.: 329717-46-6
• Molecular Formula: C₄₈H₅₆O₆Si
• Molecular Weight: 757.055

Synonyms:tert-Butyl-dimethyl-{4-[(3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-benzyloxy}-silane

Chemical Property of tert-Butyl-dimethyl-{4-[(3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-benzyloxy}-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of tert-Butyl-dimethyl-{4-[(3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-benzyloxy}-silane

There total 9 articles about tert-Butyl-dimethyl-{4-[(3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-benzyloxy}-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%

tert-Butyl-dimethyl-[4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-sulfonylmethyl)-benzyloxy]-silane (329717-45-5) → tert-Butyl-dimethyl-{4-[(3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2E)-ylidenemethyl]-benzyloxy}-silane + tert-Butyl-dimethyl-{4-[(3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-benzyloxy}-silane (329717-46-6) + {4-[Bromo-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-sulfonyl)-methyl]-benzyloxy}-tert-butyl-dimethyl-silane (329717-47-7)

Guidance literature:

With aluminum oxide; potassium hydroxide; dibromodifluoromethane; In dichloromethane; butan-1-ol; at 0 - 20 ℃;

DOI:10.1039/b008489l

Reference yield:

1,4-bis(bromomethyl)benzene (623-24-5) → tert-Butyl-dimethyl-{4-[(3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-benzyloxy}-silane (329717-46-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / NaH / tetrahydrofuran; various solvent(s) / 2 h / 20 °C

2: 60 percent / silver triflate; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 3 h / 20 °C

3: sodium methoxide; methanol / 1 h / 20 °C

4: 402 mg / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide; various solvent(s) / 8 h / 20 °C

5: 87 percent / magnesium monoperoxyphthalate hexahydrate / tetrahydrofuran; aq. ethanol / 2 h / 60 °C

6: CBr₂F₂; KOH/alumina / CH₂Cl₂; 2-methyl-propan-2-ol / 3 h / 0 - 20 °C

7: base

With methanol; aluminum oxide; potassium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; dibromodifluoromethane; sodium methylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium monoperoxyphthalate hexahydrate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/b008489l

Reference yield:

tetraacetyl thioglucose (19879-84-6) → tert-Butyl-dimethyl-{4-[(3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-benzyloxy}-silane (329717-46-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / NaH / tetrahydrofuran; various solvent(s) / 2 h / 20 °C

2: 60 percent / silver triflate; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 3 h / 20 °C

3: sodium methoxide; methanol / 1 h / 20 °C

4: 402 mg / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide; various solvent(s) / 8 h / 20 °C

5: 87 percent / magnesium monoperoxyphthalate hexahydrate / tetrahydrofuran; aq. ethanol / 2 h / 60 °C

6: CBr₂F₂; KOH/alumina / CH₂Cl₂; 2-methyl-propan-2-ol / 3 h / 0 - 20 °C

7: base

With methanol; aluminum oxide; potassium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; dibromodifluoromethane; sodium methylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium monoperoxyphthalate hexahydrate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/b008489l

upstream raw materials:

tert-Butyl-dimethyl-[4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-sulfonylmethyl)-benzyloxy]-silane

{4-[Bromo-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-sulfonyl)-methyl]-benzyloxy}-tert-butyl-dimethyl-silane

1,4-bis(bromomethyl)benzene

tetraacetyl thioglucose

Downstream raw materials:

4-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-benzaldehyde

[4-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-methanol

tert-Butyl-dimethyl-[4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-benzyloxy]-silane

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