7R,8R-dibenzyloxy-2S-{5-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanyloxy)-tetrahydropyran-2R-yl]-3-methylpent-3E-enyl}-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

Base Information

• Chemical Name: 7R,8R-dibenzyloxy-2S-{5-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanyloxy)-tetrahydropyran-2R-yl]-3-methylpent-3E-enyl}-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one
• CAS No.: 569661-02-5
• Molecular Formula: C₄₈H₇₂O₁₂Si
• Molecular Weight: 869.178

Synonyms:7R,8R-dibenzyloxy-2S-{5-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanyloxy)-tetrahydropyran-2R-yl]-3-methylpent-3E-enyl}-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

Chemical Property of 7R,8R-dibenzyloxy-2S-{5-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanyloxy)-tetrahydropyran-2R-yl]-3-methylpent-3E-enyl}-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

Chemical Property:

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Technology Process of 7R,8R-dibenzyloxy-2S-{5-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanyloxy)-tetrahydropyran-2R-yl]-3-methylpent-3E-enyl}-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

There total 1 articles about 7R,8R-dibenzyloxy-2S-{5-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanyloxy)-tetrahydropyran-2R-yl]-3-methylpent-3E-enyl}-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one 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: 65.0%

7R,8R-dibenzyloxy-2S-(2-iodoethyl)-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one (569660-81-7) + [6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-2R-(3-iodobut-2E-enyl)-4S-methoxymethoxytetrahydropyran-3R-yloxy]triethyl-silane (569660-83-9) → 7R,8R-dibenzyloxy-2S-{5-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanyloxy)-tetrahydropyran-2R-yl]-3-methylpent-3E-enyl}-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one (569661-02-5) + C48H90O12Si2

Guidance literature:

7R,8R-dibenzyloxy-2S-(2-iodoethyl)-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one; With zinc; In tetrahydrofuran; at 20 ℃; for 0.333333h;

[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-2R-(3-iodobut-2E-enyl)-4S-methoxymethoxytetrahydropyran-3R-yloxy]triethyl-silane; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; at 25 ℃; for 6h;

DOI:10.1021/ja029225v

Reference yield:

7R,8R-dibenzyloxy-2S-{5-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanyloxy)-tetrahydropyran-2R-yl]-3-methylpent-3E-enyl}-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one (569661-02-5) → C37H56O11S

Guidance literature:

Multi-step reaction with 21 steps

1.1: aq. lithium hydroxide / tetrahydrofuran / 0.33 h / 0 °C

2.1: 2.57 g / 2,6-lutidine; N-iodosuccinimide / CH₂Cl₂ / 3.5 h / 0 - 20 °C

3.1: 92 percent / 2,6-lutidine / various solvent(s) / 0.25 h / -78 °C

4.1: CH₂Cl₂; methanol / 25 h / -30 °C

5.1: LiAlH₄ / tetrahydrofuran / 0.75 h / -78 °C

6.1: oxalyl chloride; dimethylsulfoxide; diisopropylethylamine / CH₂Cl₂ / -78 - 0 °C

7.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.5 h / 0 °C

7.2: 18 percent / DMPU / tetrahydrofuran / 1.5 h / -78 - 20 °C

8.1: 83 percent / various solvent(s) / 1.33 h / 0 °C

9.1: 91 percent / aq. hydrogen peroxide; sodium bicarbonate / tetrahydrofuran / 1 h / Heating

10.1: 77 percent / Li / tetrahydrofuran; liquid ammonia; diethyl ether / -78 °C

11.1: 93 percent / tetrahydrofuran / 1 h / Heating

12.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

12.2: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 15 h / 20 °C

13.1: 85 percent / Ru[(PCy₃)(=CHPh)(N,N'-Me₂-imidazolidin-2-yl)]Cl₂ / benzene / 0.5 h / Heating

14.1: aq. sodium bicarbonate; sodium periodate / tetrahydrofuran; 2-methyl-propan-2-ol / 0.17 h

15.1: NaH / tetrahydrofuran / 0.5 h / 0 - 20 °C

15.2: 0.171 g / tetrahydrofuran / 0.5 h / 20 °C

16.1: 91 percent / H₂ / Pd(OH)2/C / ethyl acetate / 20 h

17.1: 91 percent / triethylamine; DMAP / CH₂Cl₂ / 12 h / 20 °C

18.1: 96 percent / di-iso-butylaluminum hydride / tetrahydrofuran / 0.75 h / -78 °C

19.1: CH₂Cl₂ / 1 h / 20 °C

19.2: 83 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / 25 °C

20.1: 100 percent / aq. HCl / tetrahydrofuran / 0.25 h / 20 °C

21.1: di-n-butyltin oxide / methanol / 6 h / 20 °C

21.2: 97 percent / CH₂Cl₂ / 1.5 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; lithium hydroxide; sodium periodate; N-iodo-succinimide; lithium aluminium tetrahydride; oxalyl dichloride; diisobutylaluminum hydride; Ru[(PCy₃)(=CHPh)(N,N'-Me₂-imidazolidin-2-yl)]Cl₂; potassium tert-butylate; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; lithium; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ammonia; ethyl acetate; tert-butyl alcohol; benzene; 6.1: Swern oxidation / 19.1: Peterson olefination;

DOI:10.1021/ja029225v

Reference yield:

7R,8R-dibenzyloxy-2S-{5-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanyloxy)-tetrahydropyran-2R-yl]-3-methylpent-3E-enyl}-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one (569661-02-5) → 2S-(2R,3R-bis-benzyloxy-5R-hydroxy-3R-methyl-tetrahydro-pyran-4R-yloxy)-7-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanyloxoy)-tetrahydropyran-2R-yl]-5-methylhept-5E-enoic acid (569661-65-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 0 ℃; for 0.333333h;

DOI:10.1021/ja029225v

upstream raw materials:

7R,8R-dibenzyloxy-2S-(2-iodoethyl)-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-2R-(3-iodobut-2E-enyl)-4S-methoxymethoxytetrahydropyran-3R-yloxy]triethyl-silane

Downstream raw materials:

2S-(2R,3R-bis-benzyloxy-5R-hydroxy-3R-methyl-tetrahydro-pyran-4R-yloxy)-7-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanyloxoy)-tetrahydropyran-2R-yl]-5-methylhept-5E-enoic acid

{5R,6R-dibenzyloxy-4R-[2R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-5aR-methyl-9R-vinyldodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8S-yloxy]-5R-methyltetrahydropyran-3R-yloxy}-triisopropylsilane

2R-(3S-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxytetrahydropyran-3R-ol

3S-(2R-3R-bis-benzyloxy-5-hydroxy-3R-methyltetrahydropyran-4R-yloxy)-6S-{2-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanyloxy)-tetrahydropyran-2R-yl]-1R-iodoethyl}-6S-methyl-tetrahydropyran-2-one

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