Carbonic acid (R)-5-benzyloxy-1-((R)-1-methyl-allyl)-pentyl ester tert-butyl ester

Base Information

• Chemical Name: Carbonic acid (R)-5-benzyloxy-1-((R)-1-methyl-allyl)-pentyl ester tert-butyl ester
• CAS No.: 200186-44-3
• Molecular Formula: C₂₁H₃₂O₄
• Molecular Weight: 348.483

Synonyms:Carbonic acid (R)-5-benzyloxy-1-((R)-1-methyl-allyl)-pentyl ester tert-butyl ester

Chemical Property of Carbonic acid (R)-5-benzyloxy-1-((R)-1-methyl-allyl)-pentyl ester tert-butyl ester

Chemical Property:

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Technology Process of Carbonic acid (R)-5-benzyloxy-1-((R)-1-methyl-allyl)-pentyl ester tert-butyl ester

There total 2 articles about Carbonic acid (R)-5-benzyloxy-1-((R)-1-methyl-allyl)-pentyl ester tert-butyl 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: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + (3R,4R)-8-Benzyloxy-3-methyl-oct-1-en-4-ol (200186-29-4) → Carbonic acid (R)-5-benzyloxy-1-((R)-1-methyl-allyl)-pentyl ester tert-butyl ester (200186-44-3)

Guidance literature:

(3R,4R)-8-Benzyloxy-3-methyl-oct-1-en-4-ol; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

di-tert-butyl dicarbonate; In tetrahydrofuran; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tet.2009.04.001

Reference yield:

5-benzyloxy-1-pentanal (78999-24-3) → Carbonic acid (R)-5-benzyloxy-1-((R)-1-methyl-allyl)-pentyl ester tert-butyl ester (200186-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) BF₃*OEt₂; 2.) NaOH, H₂O₂ / 1.) -78 deg C

2: 89 percent / NaHMDS / tetrahydrofuran / 0 °C

With sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide; sodium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(97)10499-3

Reference yield: 77.0%

Carbonic acid (R)-5-benzyloxy-1-((R)-1-methyl-allyl)-pentyl ester tert-butyl ester (200186-44-3) → (4R,5S,6R)-4-(4-Benzyloxy-butyl)-6-iodomethyl-5-methyl-[1,3]dioxan-2-one (200186-30-7)

Guidance literature:

With iodine(I) bromide; In dichloromethane; toluene; at -78 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.tet.2009.04.001

upstream raw materials:

di-tert-butyl dicarbonate

(3R,4R)-8-Benzyloxy-3-methyl-oct-1-en-4-ol

5-benzyloxy-1-pentanal

Downstream raw materials:

(4R,5S,6R)-4-(4-Benzyloxy-butyl)-6-iodomethyl-5-methyl-[1,3]dioxan-2-one

2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-4-benzyloxy-6-[(S)-[(2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-(tert-butyl-dimethyl-silanyloxy)-methyl]-3-hydroxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

[(S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-((4aR,6R,7R,8R,8aS)-8-benzyloxy-2,2,7-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-methoxy]-tert-butyl-dimethyl-silane

C₄₉H₉₂O₁₀Si₃

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