(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-tetrahydro-pyran-3-ol
• CAS No.: 441352-36-9
• Molecular Formula: C₅₀H₆₈O₁₀Si
• Molecular Weight: 857.169
• Mol file: 441352-36-9.mol

Synonyms:(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-tetrahydro-pyran-3-ol

Chemical Property of (2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-tetrahydro-pyran-3-ol

There total 23 articles about (2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-tetrahydro-pyran-3-ol 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:

isopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (69247-19-4,113019-32-2,23339-23-3) → (2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-tetrahydro-pyran-3-ol (441352-36-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: H₂ / 10 percent Pd/C / ethyl acetate; ethanol / 20 °C

2.1: NaOMe / methanol / 0.5 h / 20 °C

3.1: tetra-n-butylammonium iodide; NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

3.2: 5.89 g / tetrahydrofuran; dimethylformamide / 0 - 20 °C

4.1: 78 percent / aq. acetic acid; aq. HCl / 48 h / 60 °C

5.1: 78 percent / N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / acetonitrile / 4.5 h / 20 °C

6.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

6.2: tetrahydrofuran / 1.5 h / 0 °C

7.1: 9-BBN / tetrahydrofuran / 2 h / Heating

7.2: aq. Cs₂CO₃ / tetrahydrofuran / 0.25 h / 20 °C

7.3: 91 percent / Pd₂(dba)3*CHCl₃; Ph₃As / tetrahydrofuran; dimethylformamide / 14 h / 20 °C

8.1: thexylborane / tetrahydrofuran / 2 h / 0 °C

8.2: 92 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 20 - 45 °C

With hydrogenchloride; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 4 A molecular sieve; thexylborane; hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(02)00045-5

Reference yield:

D-glucal triacetate (2873-29-2) → (2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-tetrahydro-pyran-3-ol (441352-36-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: BF₃*OEt₂ / CH₂Cl₂ / 0 - 20 °C

2.1: H₂ / 10 percent Pd/C / ethyl acetate; ethanol / 20 °C

3.1: NaOMe / methanol / 0.5 h / 20 °C

4.1: tetra-n-butylammonium iodide; NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

4.2: 5.89 g / tetrahydrofuran; dimethylformamide / 0 - 20 °C

5.1: 78 percent / aq. acetic acid; aq. HCl / 48 h / 60 °C

6.1: 78 percent / N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / acetonitrile / 4.5 h / 20 °C

7.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

7.2: tetrahydrofuran / 1.5 h / 0 °C

8.1: 9-BBN / tetrahydrofuran / 2 h / Heating

8.2: aq. Cs₂CO₃ / tetrahydrofuran / 0.25 h / 20 °C

8.3: 91 percent / Pd₂(dba)3*CHCl₃; Ph₃As / tetrahydrofuran; dimethylformamide / 14 h / 20 °C

9.1: thexylborane / tetrahydrofuran / 2 h / 0 °C

9.2: 92 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 20 - 45 °C

With hydrogenchloride; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 4 A molecular sieve; thexylborane; boron trifluoride diethyl etherate; hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(02)00045-5

Reference yield:

ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate (82614-10-6) → (2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-tetrahydro-pyran-3-ol (441352-36-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

2.1: NaBH₄ / methanol / 0.5 h / 0 °C

3.1: 45.9 g / Et₃N; DMAP / CH₂Cl₂ / 20 °C

4.1: H₂ / 20 percent Pd(OH)2/C / ethyl acetate; methanol / 20 °C

5.1: 21.23 g / camphorsulfonic acid / CH₂Cl₂; dimethylformamide / 20 °C

6.1: tetra-n-butylammonium iodide; sodium bis(trimethylsilyl)amide / dimethylformamide; tetrahydrofuran / 0.08 h / 0 °C

6.2: dimethylformamide; tetrahydrofuran / 0 - 20 °C

7.1: 22.00 g / camphorsulfonic acid / CH₂Cl₂; methanol / 5 h / 20 °C

8.1: 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

9.1: 2.27 g / DIBALH / CH₂Cl₂; toluene / 2 h / -78 °C

10.1: tetra-n-butylammonium iodide; diisopropylethylamine / CH₂Cl₂ / 20 °C

11.1: 19.09 g / camphorsulfonic acid / CH₂Cl₂; methanol / 1 h / 0 °C

12.1: 100 percent / imidazole; Ph₃P; I₂ / benzene / 0.75 h / 20 °C

13.1: 96 percent / tBuOK / tetrahydrofuran / 4 h / 0 °C

14.1: 9-BBN / tetrahydrofuran / 2 h / Heating

14.2: aq. Cs₂CO₃ / tetrahydrofuran / 0.25 h / 20 °C

14.3: 91 percent / Pd₂(dba)3*CHCl₃; Ph₃As / tetrahydrofuran; dimethylformamide / 14 h / 20 °C

15.1: thexylborane / tetrahydrofuran / 2 h / 0 °C

15.2: 92 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 20 - 45 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; thexylborane; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; iodine; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4020(02)00045-5

upstream raw materials:

isopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanal

2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol

ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate

Downstream raw materials:

(2S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-dihydro-pyran-3-one

(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-2-Allyl-4,8-bis-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-ol

(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-2-Allyl-3-allyloxy-4,8-bis-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-2-Allyl-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene