(2S,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-6,7-dihydro-oxepin-3-one

Base Information

• Chemical Name: (2S,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-6,7-dihydro-oxepin-3-one
• CAS No.: 441352-42-7
• Molecular Formula: C₅₁H₆₆O₁₀Si
• Molecular Weight: 867.165

Synonyms:

Chemical Property of (2S,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-6,7-dihydro-oxepin-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-6,7-dihydro-oxepin-3-one

There total 20 articles about (2S,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-6,7-dihydro-oxepin-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:

(2R,3S,7S)-3-Benzyloxy-2-benzyloxymethyl-7-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-6-trimethylsilanyloxy-2,3,4,7-tetrahydro-oxepine → (2S,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-6,7-dihydro-oxepin-3-one (441352-42-7)

Guidance literature:

With palladium diacetate; In acetonitrile; at 20 ℃; for 0.5h;

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

Reference yield:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → (2S,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-6,7-dihydro-oxepin-3-one (441352-42-7)

Guidance literature:

Multi-step reaction with 19 steps

1.1: tetrahydrofuran / 3 h / Heating

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

3.1: 16.33 g / camphorsulfonic acid / CH₂Cl₂ / 20 °C

4.1: i-Pr₂NEt; tetra-n-butylammonium iodide / CH₂Cl₂ / 72 h / 20 °C

5.1: LiAlH₄ / tetrahydrofuran / 0.75 h / 0 °C

6.1: 20.42 g / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 - 20 °C

7.1: H₂ / 20 percent Pd/C / ethyl acetate; methanol / 20 °C

8.1: NaH / dimethylformamide / 0.5 h / 20 °C

8.2: tetra-n-butylammonium iodide / dimethylformamide / 20 °C

9.1: 14.03 g / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

10.1: Et₃N; SO₃*pyridine complex / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

11.1: BF₃*OEt₂; Me₂S / CH₂Cl₂ / 0.5 h / 0 °C

12.1: 259.0 mg / NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

13.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 °C

13.2: 64 percent / DMAP / benzene / 4 h / Heating

14.1: 75 percent / HMPA; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

15.1: aq. NaHCO₃ / tetrahydrofuran / 0.25 h / 20 °C

15.2: Pd(PPh₃)4 / tetrahydrofuran; dimethylformamide / 20 h / 50 °C

15.3: 97 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 1 h / 20 °C

16.1: 2,3-dimethyl-2-butene; BH₃*THF / tetrahydrofuran / -10 - 0 °C

16.2: 83 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 2 h / 20 °C

17.1: 99 percent / 4 Angstroem molecular sieves; N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1 h / 20 °C

18.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C

18.2: Et₃N / tetrahydrofuran / 0.17 h / -78 °C

19.1: 632.5 mg / Pd(OAc)2 / acetonitrile / 0.5 h / 20 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 2,3-Dimethyl-2-butene; borane-THF; 2-methyl-but-2-ene; pyridine-SO₃ complex; dimethylsulfide; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

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

Reference yield:

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester (116237-17-3) → (2S,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-(2-methoxymethoxy-ethyl)-tetrahydro-pyran-2-ylmethyl]-6,7-dihydro-oxepin-3-one (441352-42-7)

Guidance literature:

Multi-step reaction with 16 steps

1.1: i-Pr₂NEt; tetra-n-butylammonium iodide / CH₂Cl₂ / 72 h / 20 °C

2.1: LiAlH₄ / tetrahydrofuran / 0.75 h / 0 °C

3.1: 20.42 g / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 - 20 °C

4.1: H₂ / 20 percent Pd/C / ethyl acetate; methanol / 20 °C

5.1: NaH / dimethylformamide / 0.5 h / 20 °C

5.2: tetra-n-butylammonium iodide / dimethylformamide / 20 °C

6.1: 14.03 g / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

7.1: Et₃N; SO₃*pyridine complex / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

8.1: BF₃*OEt₂; Me₂S / CH₂Cl₂ / 0.5 h / 0 °C

9.1: 259.0 mg / NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

10.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 °C

10.2: 64 percent / DMAP / benzene / 4 h / Heating

11.1: 75 percent / HMPA; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

12.1: aq. NaHCO₃ / tetrahydrofuran / 0.25 h / 20 °C

12.2: Pd(PPh₃)4 / tetrahydrofuran; dimethylformamide / 20 h / 50 °C

12.3: 97 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 1 h / 20 °C

13.1: 2,3-dimethyl-2-butene; BH₃*THF / tetrahydrofuran / -10 - 0 °C

13.2: 83 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 2 h / 20 °C

14.1: 99 percent / 4 Angstroem molecular sieves; N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1 h / 20 °C

15.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C

15.2: Et₃N / tetrahydrofuran / 0.17 h / -78 °C

16.1: 632.5 mg / Pd(OAc)2 / acetonitrile / 0.5 h / 20 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 2,3-Dimethyl-2-butene; borane-THF; 2-methyl-but-2-ene; pyridine-SO₃ complex; dimethylsulfide; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

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

upstream raw materials:

2-deoxy-D-ribose

benzyl bromide

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

5(S), 6(R), 7-trihydroxyheptanoic acid methyl ester

Downstream raw materials:

2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-Tris-benzyloxy-9-benzyloxymethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethanol

(2R,4aR,5aS,6aR,8S,9R,10R,10aS,11aR,13aS)-8-Allyl-2-(4-methoxy-phenyl)-4a,5a,6,6a,8,9,10,10a,11a,13a-decahydro-4H-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalene-9,10-diol

[(2R,4aR,5aS,6aR,8S,9S,10R,10aR,11aR,13aS)-8-Allyl-9-allyloxy-2-(4-methoxy-phenyl)-4a,5a,6,6a,8,9,10,10a,11a,13a-decahydro-4H-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-10-yloxy]-triisopropyl-silane

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

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