(2S,3S,4R,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4R,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 356068-06-9
• Molecular Formula: C₃₂H₄₄O₈Si
• Molecular Weight: 584.782

Synonyms:(2S,3S,4R,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4R,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 13 articles about (2S,3S,4R,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester 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:

methyl 3,4-di-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranuronate (57690-62-7) → (2S,3S,4R,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester (356068-06-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 98 percent / NaOMe / methanol / -20 °C

2.1: Bu₂SnO / benzene / 5 h / Heating

2.2: 27 percent / Bu₄NI / benzene / 8 h / Heating

3.1: 89 percent / 2,6-lutidine / CH₂Cl₂

4.1: DMDO / acetone / 0 °C

4.2: 82 percent / ZnCl₂ / CH₂Cl₂

5.1: DMAP / CH₂Cl₂

With 2,6-dimethylpyridine; dmap; sodium methylate; di(n-butyl)tin oxide; In methanol; dichloromethane; acetone; benzene;

DOI:10.1016/S0040-4039(01)00607-4

Reference yield:

3-O-benzyl-D-glucopyranose (65877-63-6,97590-76-6,99396-09-5,5531-09-9) → (2S,3S,4R,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester (356068-06-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pyridine / 80 °C

2.1: pyridine

3.1: CrO₃; 3M H₂SO₄ / acetone

4.1: CH₂Cl₂; methanol

5.1: 76 percent / hydrazine acetate / dimethylformamide

6.1: 71 percent / P(OPh)3; Br₂ / pyridine; CH₂Cl₂

7.1: 90 percent / Zn; vitamin B₁₂; NH₄Cl / methanol

8.1: 90 percent / NaOMe / methanol / -20 °C

9.1: 89 percent / 2,6-lutidine / CH₂Cl₂

10.1: DMDO / acetone / 0 °C

10.2: 82 percent / ZnCl₂ / CH₂Cl₂

11.1: DMAP / CH₂Cl₂

With 2,6-dimethylpyridine; chromium(VI) oxide; triphenyl phosphite; dmap; cyanocobalamin; sulfuric acid; bromine; sodium methylate; hydrazinium monoacetate; ammonium chloride; zinc; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(01)00607-4

Reference yield:

O1,O2,O4-Triacetyl-O3-benzyl-O6-trityl-ξ-D-glucopyranose (66963-59-5) → (2S,3S,4R,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester (356068-06-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: CrO₃; 3M H₂SO₄ / acetone

2.1: CH₂Cl₂; methanol

3.1: 76 percent / hydrazine acetate / dimethylformamide

4.1: 71 percent / P(OPh)3; Br₂ / pyridine; CH₂Cl₂

5.1: 90 percent / Zn; vitamin B₁₂; NH₄Cl / methanol

6.1: 90 percent / NaOMe / methanol / -20 °C

7.1: 89 percent / 2,6-lutidine / CH₂Cl₂

8.1: DMDO / acetone / 0 °C

8.2: 82 percent / ZnCl₂ / CH₂Cl₂

9.1: DMAP / CH₂Cl₂

With 2,6-dimethylpyridine; chromium(VI) oxide; triphenyl phosphite; dmap; cyanocobalamin; sulfuric acid; bromine; sodium methylate; hydrazinium monoacetate; ammonium chloride; zinc; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(01)00607-4

upstream raw materials:

methyl 3,4-di-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranuronate

3-O-benzyl-D-glucopyranose

O¹,O²,O⁴-Triacetyl-O³-benzyl-O⁶-trityl-ξ-D-glucopyranose

methyl 1,2-dideoxy-D-arabino-hex-1-enopyranuronate

Downstream raw materials:

methyl (n-pentenyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosid)-uronate

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