Benzoic acid (S)-2-[(4R,5S,6R)-6-((1R,3R)-3-{(4S,5S,6R)-6-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-1-hydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl ester

Base Information

• Chemical Name: Benzoic acid (S)-2-[(4R,5S,6R)-6-((1R,3R)-3-{(4S,5S,6R)-6-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-1-hydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl ester
• CAS No.: 133782-40-8
• Molecular Formula: C₄₀H₇₀O₉Si
• Molecular Weight: 723.076

Synonyms:

Chemical Property of Benzoic acid (S)-2-[(4R,5S,6R)-6-((1R,3R)-3-{(4S,5S,6R)-6-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-1-hydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of Benzoic acid (S)-2-[(4R,5S,6R)-6-((1R,3R)-3-{(4S,5S,6R)-6-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-1-hydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl ester

There total 15 articles about Benzoic acid (S)-2-[(4R,5S,6R)-6-((1R,3R)-3-{(4S,5S,6R)-6-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-1-hydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl 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:

t-butyldimethylsiyl triflate (69739-34-0) + Benzoic acid (S)-2-((4R,5S,6R)-6-{(1R,3R)-3-[(4S,5S,6R)-6-((1R,2R)-1,2-dihydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-hydroxy-1-methyl-butyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propyl ester → Benzoic acid (S)-2-[(4R,5S,6R)-6-((1R,3R)-3-{(4S,5S,6R)-6-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-1-hydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl ester (133782-40-8)

Guidance literature:

With ethyl azide; In dichloromethane; at -20 - 20 ℃; for 0.25h; Yield given;

DOI:10.1016/S0040-4020(01)96140-X

Reference yield:

(4R,6R)-6-Benzyloxy-4-methyl-6-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-heptan-3-one (114114-23-7) → Benzoic acid (S)-2-[(4R,5S,6R)-6-((1R,3R)-3-{(4S,5S,6R)-6-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-1-hydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl ester (133782-40-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) HMDS, BuLi / 1) THF, hexane, 3 h, -60 deg C 2) THF, 15 min, -78 deg C

2: 0.032 g / LiAlH(t-BuO)3 / diethyl ether

3: 86 percent / DMP, (+/-)-10-camphorosulfonic acid / 0.67 h / 20 °C

4: m-CPBA / tetrahydrofuran / 0.5 h / 20 °C

5: 68 percent / 2,2-dithio-bis(4-t-butyl-1-isopropylimidazole), PPh₃ / toluene / 20 h / Heating

6: 95 percent / LiAlH₄ / diethyl ether / 1.5 h / -50 deg C to r.t.

7: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

8: EtN₃ / CH₂Cl₂ / 0.25 h / -20 - 20 °C

With pyridine; lithium aluminium tetrahydride; n-butyllithium; phthalic acid dimethyl ester; 10-camphorsufonic acid; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; bis(4-tert-butyl-1-iso-propyl-1H-imidazol-2-yl)disulfide; ethyl azide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)96140-X

Reference yield:

(2R,3R)-2-((4R,5S,6S)-6-{(1R,3R)-3-Hydroxy-3-[(4R,5S,6R)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-methyl-butyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentane-2,3-diol (133800-69-8) → Benzoic acid (S)-2-[(4R,5S,6R)-6-((1R,3R)-3-{(4S,5S,6R)-6-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-1-hydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propyl ester (133782-40-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

2: EtN₃ / CH₂Cl₂ / 0.25 h / -20 - 20 °C

With pyridine; ethyl azide; In dichloromethane;

DOI:10.1016/S0040-4020(01)96140-X

upstream raw materials:

t-butyldimethylsiyl triflate

(4R,6R)-6-Benzyloxy-4-methyl-6-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-heptan-3-one

(2R,3R)-2-((4R,5S,6S)-6-{(1R,3R)-3-Hydroxy-3-[(4R,5S,6R)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-methyl-butyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentane-2,3-diol

(R)-2-((4S,5S,6R)-6-{(1R,3R)-3-[(4S,5S,6R)-6-((1R,2R)-1,2-Dihydroxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-hydroxy-1-methyl-butyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionaldehyde

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