(4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,5,6-tris-methoxymethoxy-cyclohex-2-enone

Base Information

• Chemical Name: (4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,5,6-tris-methoxymethoxy-cyclohex-2-enone
• CAS No.: 494860-30-9
• Molecular Formula: C₂₉H₄₀O₈Si
• Molecular Weight: 544.717

Synonyms:(4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,5,6-tris-methoxymethoxy-cyclohex-2-enone

Chemical Property of (4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,5,6-tris-methoxymethoxy-cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,5,6-tris-methoxymethoxy-cyclohex-2-enone

There total 6 articles about (4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,5,6-tris-methoxymethoxy-cyclohex-2-enone 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: 70.0%

[(3S,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-ylmethyl]-phosphonic acid dimethyl ester → (4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,5,6-tris-methoxymethoxy-cyclohex-2-enone (494860-30-9)

Guidance literature:

[(3S,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-ylmethyl]-phosphonic acid dimethyl ester; With sodium tetrahydroborate; In tetrahydrofuran;

With dimethyl sulfoxide; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; at -78 ℃;

With sodium hydride; In tetrahydrofuran; dichloromethane; diethylene glycol dimethyl ether; at 65 ℃;

DOI:10.1002/1521-3773(20020816)41:16<3041::AID-ANIE3041>3.0.CO;2-V

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,5,6-tris-methoxymethoxy-cyclohex-2-enone (494860-30-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 86 percent / 4-dimethylaminopyridine; pyridine

2.1: 88 percent / diisopropylethylamine; 4-dimethylaminopyridine / CH₂Cl₂

3.1: ceric ammonium nitrate / acetonitrile; H₂O

4.1: dimethylsulfoxide; acetic anhydride

5.1: 82 percent / n-BuLi / tetrahydrofuran

6.1: NaBH₄ / tetrahydrofuran

6.2: dimethylsulfoxide; trifluoroacetic anhydride / tetrahydrofuran; CH₂Cl₂ / -78 °C

6.3: 70 percent / NaH / tetrahydrofuran; CH₂Cl₂; bis-(2-methoxy-ethyl) ether / 65 °C

With pyridine; dmap; sodium tetrahydroborate; n-butyllithium; ammonium cerium(IV) nitrate; acetic anhydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; acetonitrile; 4.1: Albright-Goldman oxidation;

DOI:10.1002/1521-3773(20020816)41:16<3041::AID-ANIE3041>3.0.CO;2-V

Reference yield:

(3S,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-one (494860-25-2) → (4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,5,6-tris-methoxymethoxy-cyclohex-2-enone (494860-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 82 percent / n-BuLi / tetrahydrofuran

2.1: NaBH₄ / tetrahydrofuran

2.2: dimethylsulfoxide; trifluoroacetic anhydride / tetrahydrofuran; CH₂Cl₂ / -78 °C

2.3: 70 percent / NaH / tetrahydrofuran; CH₂Cl₂; bis-(2-methoxy-ethyl) ether / 65 °C

With sodium tetrahydroborate; n-butyllithium; In tetrahydrofuran;

DOI:10.1002/1521-3773(20020816)41:16<3041::AID-ANIE3041>3.0.CO;2-V

upstream raw materials:

tert-butylchlorodiphenylsilane

(3S,4S,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-one

4-methoxyphenyl 6-O-TBDPS-1-α-D-mannopyranoside

tert-Butyl-diphenyl-[(2R,3R,4S,5S,6R)-3,4,5-tris-methoxymethoxy-6-(4-methoxy-phenoxy)-tetrahydro-pyran-2-ylmethoxy]-silane

Downstream raw materials:

((3R,4R,5S,6R)-3-Methoxy-4,5,6-tris-methoxymethoxy-cyclohex-1-enyl)-methanol

tert-Butyl-((3R,4R,5S,6R)-3-methoxy-4,5,6-tris-methoxymethoxy-cyclohex-1-enylmethoxy)-diphenyl-silane

Phosphoric acid dibenzyl ester (3R,4R,5S,6R)-3-methoxy-4,5,6-tris-methoxymethoxy-cyclohex-1-enylmethyl ester

(1R,4R,5S,6R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,5,6-tris-methoxymethoxy-cyclohex-2-enol

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