3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose

Base Information

• Chemical Name: 3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose
• CAS No.: 871348-24-2
• Molecular Formula: C₂₉H₅₂O₇SSi₂
• Molecular Weight: 600.965

Synonyms:3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose

Chemical Property of 3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose

Chemical Property:

• Boiling Point: 597.9±48.0 °C(Predicted)
• PSA: 96.51000
• Density: 1.07±0.1 g/cm3(Predicted)
• LogP: 7.33100

Purity/Quality:

99% ^*data from raw suppliers

3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose, is an intermediate in the synthesis of in the synthesis of Eribulin mesylate (E615203), a synthetic analog of the marine natural product halichondrin B.

Technology Process of 3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose

There total 14 articles about 3,6-Anhydro-2,4,7-trideoxy-8,9-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-methyl-4-[(phenylsulfonyl)methyl]-D-glycero-D-gulo-nonose 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: 89.0%

C30H54O6SSi2 (871348-22-0) → 2-((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)acetaldehyde (871348-24-2)

Guidance literature:

C₃₀H₅₄O₆SSi₂; With ozone; In isopropyl alcohol; at 50 ℃;

With 2,6-di-tert-butyl-4-methyl-phenol; hydrogen; In isopropyl alcohol; at 15 ℃;

DOI:10.1055/s-0032-1317920

Reference yield:

diethyl phenylsulfonylmethylphosphonate (56069-39-7) → 2-((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)acetaldehyde (871348-24-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium hexamethyldisilazane / toluene; tetrahydrofuran / 0 - 20 °C

2.1: trimethylsilyl iodide / toluene; acetonitrile / 60 °C

3.1: sodium tris(acetoxy)borohydride; tetrabutyl-ammonium chloride / toluene; 1,2-dimethoxyethane / 80 °C

4.1: potassium carbonate / methanol / 50 °C

5.1: sulfuric acid / 1,2-dimethoxyethane / 40 °C

6.1: sodium t-butanolate / 1,2-dimethoxyethane; 1-methyl-pyrrolidin-2-one / 10 °C

7.1: hydrogenchloride / methanol / 25 °C

8.1: 1H-imidazole / N,N-dimethyl-formamide / 25 °C

9.1: ozone / isopropyl alcohol / 50 °C

9.2: Lindlar’s catalyst / 15 °C

With 1H-imidazole; hydrogenchloride; trimethylsilyl iodide; sulfuric acid; tetrabutyl-ammonium chloride; sodium tris(acetoxy)borohydride; potassium carbonate; ozone; lithium hexamethyldisilazane; sodium t-butanolate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; 1,2-dimethoxyethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1055/s-0032-1317920

Reference yield:

3-[(3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propane-1,2-diol → 2-((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)acetaldehyde (871348-24-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: dmap; 4-methyl-morpholine / toluene / 75 °C

2.1: titanium tetrachloride; titanium(IV) isopropylate / toluene / 25 °C

3.1: trichloroacetic acid anhydride; triethylamine / toluene; dimethyl sulfoxide / -10 °C

4.1: lithium hexamethyldisilazane / toluene; tetrahydrofuran / 0 - 20 °C

5.1: trimethylsilyl iodide / toluene; acetonitrile / 60 °C

6.1: sodium tris(acetoxy)borohydride; tetrabutyl-ammonium chloride / toluene; 1,2-dimethoxyethane / 80 °C

7.1: potassium carbonate / methanol / 50 °C

8.1: sulfuric acid / 1,2-dimethoxyethane / 40 °C

9.1: sodium t-butanolate / 1,2-dimethoxyethane; 1-methyl-pyrrolidin-2-one / 10 °C

10.1: hydrogenchloride / methanol / 25 °C

11.1: 1H-imidazole / N,N-dimethyl-formamide / 25 °C

12.1: ozone / isopropyl alcohol / 50 °C

12.2: Lindlar’s catalyst / 15 °C

With 4-methyl-morpholine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; dmap; trimethylsilyl iodide; sulfuric acid; tetrabutyl-ammonium chloride; titanium tetrachloride; sodium tris(acetoxy)borohydride; potassium carbonate; ozone; triethylamine; lithium hexamethyldisilazane; sodium t-butanolate; trichloroacetic acid anhydride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; 1,2-dimethoxyethane; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; 3.1: |Swern Oxidation;

DOI:10.1055/s-0032-1317920

upstream raw materials:

C₃₀H₅₄O₆SSi₂

diethyl phenylsulfonylmethylphosphonate

C₃₁H₃₂O₈

[(2S)-3-[(2R,3R,4S,5S)-5-allyl-3-benzyloxy-4-hydroxytetrahydrofuran-2-yl]-2-benzoyloxypropyl]benzoate

Downstream raw materials:

C₅₃H₈₅IO₁₂SSi₂

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