(S)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-yn-2-ol

Base Information

• Chemical Name: (S)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-yn-2-ol
• CAS No.: 107148-30-1
• Molecular Formula: C₃₁H₄₂O₅Si
• Molecular Weight: 522.757
• Mol file: 107148-30-1.mol

Synonyms:(S)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-yn-2-ol

Chemical Property of (S)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-yn-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-yn-2-ol

There total 24 articles about (S)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-yn-2-ol 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: 93.0%

<3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one (107148-29-8) → (R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-yn-2-ol (107148-30-1)

Guidance literature:

With (-)-(S)-alpine-borane; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1021/jo00253a021

Reference yield: 85.0%

<3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one (107148-29-8) → (S)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-yn-2-ol (107148-30-1)

Guidance literature:

With R-B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1021/jo00253a021

Reference yield:

(5S-cis)-5,6-dihydro-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-ol (107148-23-2) → (R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-yn-2-ol (107148-30-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / xylene

2: 90 percent / OsO₄, NMO

3: 90 percent / p-TsOH

4: 96 percent / BF₃*Et₂O / tetrahydrofuran / -78 °C

5: 88 percent / (R)-alpineborane / tetrahydrofuran / 25 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In tetrahydrofuran; xylene;

DOI:10.1021/jo00383a046

upstream raw materials:

<3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one

2-{(3S,4R,5R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide

<3aR-(3aα,4α,7α,7aα)>-tetrahydro-N,N,2,2-tetramethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetamide

3,5-hexadienoyl chloride

Downstream raw materials:

<3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol

pseudomonic acid C

(E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol

(3aS,4S,7S,7aR)-7-[(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodo-4-methyl-hex-2-enyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran