2-(tert-Butyl-diphenyl-silanyloxy)-6-[(2S,4R,6R)-4-(2-chloro-acetoxy)-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-benzoic acid methyl ester

Base Information

• Chemical Name: 2-(tert-Butyl-diphenyl-silanyloxy)-6-[(2S,4R,6R)-4-(2-chloro-acetoxy)-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-benzoic acid methyl ester
• CAS No.: 674336-02-8
• Molecular Formula: C₃₄H₄₁ClO₇Si
• Molecular Weight: 625.234

Synonyms:2-(tert-Butyl-diphenyl-silanyloxy)-6-[(2S,4R,6R)-4-(2-chloro-acetoxy)-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-benzoic acid methyl ester

Chemical Property of 2-(tert-Butyl-diphenyl-silanyloxy)-6-[(2S,4R,6R)-4-(2-chloro-acetoxy)-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-benzoic acid methyl ester

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Technology Process of 2-(tert-Butyl-diphenyl-silanyloxy)-6-[(2S,4R,6R)-4-(2-chloro-acetoxy)-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-benzoic acid methyl ester

There total 2 articles about 2-(tert-Butyl-diphenyl-silanyloxy)-6-[(2S,4R,6R)-4-(2-chloro-acetoxy)-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-benzoic 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: 70.0%

chloroacetic acid (79-11-8) + 2-(tert-Butyl-diphenyl-silanyloxy)-6-((2S,4S,6R)-4-hydroxy-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl)-benzoic acid methyl ester (674336-01-7) → 2-(tert-Butyl-diphenyl-silanyloxy)-6-[(2S,4R,6R)-4-(2-chloro-acetoxy)-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-benzoic acid methyl ester (674336-02-8)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 0 - 25 ℃; for 16h;

DOI:10.1021/ja037957x

Reference yield:

2-(tert-Butyl-diphenyl-silanyloxy)-6-((2S,4S)-2-methoxymethyl-3,7-dioxa-bicyclo[4.1.0]hept-4-ylmethyl)-benzoic acid methyl ester → 2-(tert-Butyl-diphenyl-silanyloxy)-6-[(2S,4R,6R)-4-(2-chloro-acetoxy)-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-benzoic acid methyl ester (674336-02-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / DIBAL-H / CH₂Cl₂ / 0.67 h / -78 °C

2: 70 percent / PPh₃; DIAD / toluene / 16 h / 0 - 25 °C

With di-isopropyl azodicarboxylate; diisobutylaluminium hydride; triphenylphosphine; In dichloromethane; toluene; 2: Mitsunobu reaction;

DOI:10.1021/ja037957x

Reference yield: 88.0%

2-(tert-Butyl-diphenyl-silanyloxy)-6-[(2S,4R,6R)-4-(2-chloro-acetoxy)-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-benzoic acid methyl ester (674336-02-8) → 2-(tert-Butyl-diphenyl-silanyloxy)-6-[(2S,4R,6R)-4-(2-chloro-acetoxy)-6-hydroxymethyl-tetrahydro-pyran-2-ylmethyl]-benzoic acid methyl ester (674336-17-5)

Guidance literature:

With 15-crown-5; boron tribromide; sodium iodide; In dichloromethane; at -30 ℃; for 1h;

DOI:10.1021/ja037957x

upstream raw materials:

chloroacetic acid

2-(tert-Butyl-diphenyl-silanyloxy)-6-((2S,4S,6R)-4-hydroxy-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl)-benzoic acid methyl ester

Downstream raw materials:

2-(tert-Butyl-diphenyl-silanyloxy)-6-[(2S,4R,6R)-4-(2-chloro-acetoxy)-6-hydroxymethyl-tetrahydro-pyran-2-ylmethyl]-benzoic acid methyl ester

((1S,11R,13R,15R)-15-Benzyloxy-7-methoxymethoxy-9-oxo-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3⁽⁸⁾,4,6-trien-11-yl)-acetaldehyde

(1S,11S,13R,15R)-11-Allyl-15-benzyloxy-7-methoxymethoxy-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3⁽⁸⁾,4,6-trien-9-one

2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid

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