4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane

Base Information

• Chemical Name: 4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane
• CAS No.: 605668-78-8
• Molecular Formula: C₂₂H₂₇BrO₄S
• Molecular Weight: 467.424

Synonyms:4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane

Chemical Property of 4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane

Chemical Property:

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Technology Process of 4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane

There total 3 articles about 4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane 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: 86.0%

2,2-dimethoxy-propane (77-76-9) + 5-benzyloxy-4-bromo-1-(SS)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol (605668-77-7) → 4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(SS)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane (605668-78-8)

Guidance literature:

With camphor-10-sulfonic acid; In acetone; at 20 ℃; for 2h;

DOI:10.1016/S0957-4166(03)00427-0 DOI:10.1016/S0040-4039(03)01650-2

Reference yield:

5-benzyloxy-1-(SR)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol (110426-22-7) → 4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(SS)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane (605668-78-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / NBS; H₂O / toluene / 0.25 h / 20 °C

2: 86 percent / CSA / acetone / 2 h / 20 °C

With N-Bromosuccinimide; camphor-10-sulfonic acid; water; In acetone; toluene;

DOI:10.1016/S0040-4039(03)01650-2

Reference yield:

(E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one (110426-21-6) → 4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(SS)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane (605668-78-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / DIBAH; ZnCl₂ / tetrahydrofuran / 0.5 h / -78 °C

2: 88 percent / NBS; H₂O / toluene / 0.25 h / 20 °C

3: 86 percent / CSA / acetone / 2 h / 20 °C

With N-Bromosuccinimide; camphor-10-sulfonic acid; water; diisobutylaluminium hydride; zinc(II) chloride; In tetrahydrofuran; acetone; toluene;

DOI:10.1016/S0040-4039(03)01650-2

upstream raw materials:

2,2-dimethoxy-propane

5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol

(E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one

5-benzyloxy-1-(S_R)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol

Downstream raw materials:

tert-butoxycarbonylamino-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid

[(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane

{1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl}-carbamic acid tert-butyl ester

[(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

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