[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2,8a-dimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2,8a-dimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-tert-butyl-dimethyl-silane
• CAS No.: 378742-02-0
• Molecular Formula: C₃₅H₅₂O₅Si
• Molecular Weight: 580.88

Synonyms:[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2,8a-dimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2,8a-dimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2,8a-dimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-tert-butyl-dimethyl-silane

There total 23 articles about [(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2,8a-dimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-tert-butyl-dimethyl-silane 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: 90.0%

(2S,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-carbaldehyde (486394-94-9) → [(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2,8a-dimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-tert-butyl-dimethyl-silane (378742-02-0)

Guidance literature:

In tetrahydrofuran; toluene; at 0 ℃; for 0.5h;

DOI:10.1021/ol0166597 DOI:10.1021/ja028167a

Reference yield:

tert-Butyl-((2R,4aR,6S,7R,8aS)-4a,6-dimethyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane (131311-03-0) → [(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2,8a-dimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-tert-butyl-dimethyl-silane (378742-02-0)

Guidance literature:

Multi-step reaction with 22 steps

1.1: OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 20 °C

1.2: NaIO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 1 h / 20 °C

2.1: potassium t-butoxide / tetrahydrofuran / 1 h / 0 - 20 °C

2.2: 6.01 g / tetrahydrofuran / 2 h / -78 - 0 °C

3.1: 5.49 g / DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

4.1: (-)-diethyl tartrate; Ti(Oi-Pr)4; 4 Angstroem molecular sievws / CH₂Cl₂ / 0.5 h / -28 °C

4.2: 1.81 g / t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / 20 h / -28 °C

5.1: 100 percent / Red-Al / tetrahydrofuran; toluene / 1.5 h / 0 °C

6.1: piridinium p-toluenesulfonate / CH₂Cl₂ / 0.67 h / 20 °C

7.1: 4.50 g / DIBALH / CH₂Cl₂; hexane / 0.75 h / 0 °C

8.1: SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0.75 h / 0 °C

9.1: 0.92 g / toluene / 2.67 h / 80 °C

10.1: 91 percent / tetra-n-butylammonium fluoride; AcOH / tetrahydrofuran / 20 - 40 °C

11.1: 86 percent / NaH / tetrahydrofuran / 1 h / 20 °C

12.1: DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

13.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

13.2: 1.07 g / tetrahydrofuran / 0.25 h / 0 °C

14.1: 9-BBN-H / tetrahydrofuran / 20 °C

14.2: aq. NaHCO₃; aq. H₂O₂ / tetrahydrofuran / 6 h / 20 °C

15.1: potassium t-butoxide / tetrahydrofuran / 0.17 h

15.2: 1.15 g / tetra-n-butylammonium iodide / tetrahydrofuran / 1.5 h / 20 °C

16.1: DDQ / CH₂Cl₂; aq. phosphate buffer / 0.67 h / 20 °C / pH 7

17.1: potassium t-butoxide / tetrahydrofuran / 0.33 h

17.2: 361.0 mg / tetra-n-butylammonium iodide / tetrahydrofuran / 0.5 h / 20 °C

18.1: 95 percent / p-TsOH*H₂O / methanol; CHCl₃ / 7 h / 20 °C

19.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

20.1: 650.1 mg / CSA / methanol / 2.75 h / 20 °C

21.1: 95 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; 4 angstroem molecular sieves / CH₂Cl₂ / 20 °C

22.1: 90 percent / tetrahydrofuran; toluene / 0.5 h / 0 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; pyridine-SO₃ complex; 4 A molecular sieve; 4 Angstroem molecular sievws; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; (-)-diethyl tartrate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; toluene; tert-butyl alcohol; 2.1: Horner-Wadsworth-Emmons reaction / 4.1: Sharpless asymmetric epoxidation / 13.1: Wittig methylenation;

DOI:10.1021/ja028167a

Reference yield:

(E)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-prop-2-en-1-ol (378741-92-5) → [(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2,8a-dimethyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-yloxy]-tert-butyl-dimethyl-silane (378742-02-0)

Guidance literature:

Multi-step reaction with 19 steps

1.1: (-)-diethyl tartrate; Ti(Oi-Pr)4; 4 Angstroem molecular sievws / CH₂Cl₂ / 0.5 h / -28 °C

1.2: 1.81 g / t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / 20 h / -28 °C

2.1: 100 percent / Red-Al / tetrahydrofuran; toluene / 1.5 h / 0 °C

3.1: piridinium p-toluenesulfonate / CH₂Cl₂ / 0.67 h / 20 °C

4.1: 4.50 g / DIBALH / CH₂Cl₂; hexane / 0.75 h / 0 °C

5.1: SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0.75 h / 0 °C

6.1: 0.92 g / toluene / 2.67 h / 80 °C

7.1: 91 percent / tetra-n-butylammonium fluoride; AcOH / tetrahydrofuran / 20 - 40 °C

8.1: 86 percent / NaH / tetrahydrofuran / 1 h / 20 °C

9.1: DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

10.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

10.2: 1.07 g / tetrahydrofuran / 0.25 h / 0 °C

11.1: 9-BBN-H / tetrahydrofuran / 20 °C

11.2: aq. NaHCO₃; aq. H₂O₂ / tetrahydrofuran / 6 h / 20 °C

12.1: potassium t-butoxide / tetrahydrofuran / 0.17 h

12.2: 1.15 g / tetra-n-butylammonium iodide / tetrahydrofuran / 1.5 h / 20 °C

13.1: DDQ / CH₂Cl₂; aq. phosphate buffer / 0.67 h / 20 °C / pH 7

14.1: potassium t-butoxide / tetrahydrofuran / 0.33 h

14.2: 361.0 mg / tetra-n-butylammonium iodide / tetrahydrofuran / 0.5 h / 20 °C

15.1: 95 percent / p-TsOH*H₂O / methanol; CHCl₃ / 7 h / 20 °C

16.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

17.1: 650.1 mg / CSA / methanol / 2.75 h / 20 °C

18.1: 95 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; 4 angstroem molecular sieves / CH₂Cl₂ / 20 °C

19.1: 90 percent / tetrahydrofuran; toluene / 0.5 h / 0 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; pyridine-SO₃ complex; 4 A molecular sieve; 4 Angstroem molecular sievws; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; (-)-diethyl tartrate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; chloroform; dimethyl sulfoxide; toluene; 1.1: Sharpless asymmetric epoxidation / 10.1: Wittig methylenation;

DOI:10.1021/ja028167a

upstream raw materials:

(2S,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-carbaldehyde

tert-Butyl-((2R,4aR,6S,7R,8aS)-4a,6-dimethyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane

(2R,4aR,6R,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde

(E)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-prop-2-en-1-ol

Downstream raw materials:

[(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetaldehyde

[(2R,3S,4aR,5S,7S,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-4a,10a-dimethyl-decahydro-1,8,10-trioxa-anthracen-2-yl]-acetic acid

[5-benzyloxy-7-(3-benzyloxy-propyl)-3-hydroxy-4a,10a-dimethyl-decahydro-1,8,10-trioxa-anthracen-2-yl]-acetic acid 9,10a-dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-yl ester

9-[10-benzyloxy-8-(3-benzyloxy-propyl)-10a,11a-dimethyl-2-vinyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-yloxy]-9,10a-dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalene

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