{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

Base Information

Chemical Name:{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
CAS No.:569661-07-0
Molecular Formula:C₅₃H₈₂O₁₂Si
Molecular Weight:939.312
Hs Code.:

{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

Synonyms:{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

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Chemical Property of {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

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Technology Process of {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

There total 11 articles about {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 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: 91.0%

: 569661-06-9
{5R,6R-dibenzyloxy-4R-[2R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-5aR-methyl-9S-(1S-phenylselanylethyl)-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8S-yloxy]-5R-methyltetrahydropyran-3R-yloxy}-triisopropyl-silane

: 569661-07-0
{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

Guidance literature:: With dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; for 1h; Heating;
DOI:10.1021/ja029225v

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 569661-07-0
{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

Guidance literature:: Multi-step reaction with 7 steps

1.1: 92 percent / 2,6-lutidine / various solvent(s) / 0.25 h / -78 °C

2.1: CH₂Cl₂; methanol / 25 h / -30 °C

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

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

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

5.2: 18 percent / DMPU / tetrahydrofuran / 1.5 h / -78 - 20 °C

6.1: 83 percent / various solvent(s) / 1.33 h / 0 °C

7.1: 91 percent / aq. hydrogen peroxide; sodium bicarbonate / tetrahydrofuran / 1 h / Heating

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; dihydrogen peroxide; sodium hexamethyldisilazane; sodium hydrogencarbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; 4.1: Swern oxidation;
DOI:10.1021/ja029225v

Reference yield:

: 569661-65-0
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

: 569661-07-0
{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

Guidance literature:: Multi-step reaction with 8 steps

1.1: 2.57 g / 2,6-lutidine; N-iodosuccinimide / CH₂Cl₂ / 3.5 h / 0 - 20 °C

2.1: 92 percent / 2,6-lutidine / various solvent(s) / 0.25 h / -78 °C

3.1: CH₂Cl₂; methanol / 25 h / -30 °C

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

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

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

6.2: 18 percent / DMPU / tetrahydrofuran / 1.5 h / -78 - 20 °C

7.1: 83 percent / various solvent(s) / 1.33 h / 0 °C

8.1: 91 percent / aq. hydrogen peroxide; sodium bicarbonate / tetrahydrofuran / 1 h / Heating

With 2,6-dimethylpyridine; N-iodo-succinimide; lithium aluminium tetrahydride; oxalyl dichloride; dihydrogen peroxide; sodium hexamethyldisilazane; sodium hydrogencarbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; 5.1: Swern oxidation;
DOI:10.1021/ja029225v