(2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7R,8R,9S,10S)-8-hydroxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one

Base Information

Chemical Name:(2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7R,8R,9S,10S)-8-hydroxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one
CAS No.:253172-24-6
Molecular Formula:C₄₆H₆₀O₉
Molecular Weight:756.977
Hs Code.:

(2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7R,8R,9S,10S)-8-hydroxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one

Synonyms:(2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7R,8R,9S,10S)-8-hydroxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one

Suppliers and Price of (2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7R,8R,9S,10S)-8-hydroxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one

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Chemical Property of (2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7R,8R,9S,10S)-8-hydroxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one

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Technology Process of (2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7R,8R,9S,10S)-8-hydroxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one

There total 27 articles about (2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7R,8R,9S,10S)-8-hydroxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-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: 30.0%

: 261776-54-9
(2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7S,8R,9S,10S)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one

: 253172-24-6
(2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7R,8R,9S,10S)-8-hydroxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one

: 253172-25-7
C₄₆H₆₀O₉

Guidance literature:: With trimethylsilyl bromide; In dichloromethane; at -78 - -50 ℃; Title compound not separated from byproducts;
DOI:10.1039/a906834a

Reference yield:

: 261776-53-8
(2S,3S)-3-Benzyloxy-3-((5R,7S,8R,9S,10S)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-2-methyl-propionic acid

: 253172-24-6
(2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7R,8R,9S,10S)-8-hydroxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 75 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine; 10-camphorsulfonic acid / CH₂Cl₂ / 24 h / 35 °C

2.1: 63 percent / tetrahydrofuran / 60 °C

3.1: BH₃*THF / tetrahydrofuran / 0 - 20 °C

3.2: 75 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

4.1: 57 percent / DMSO; (COCl)2; triethylamine / CH₂Cl₂ / 1.5 h / -70 - -40 °C

5.1: 58 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 12 h / 20 °C

6.1: trimethylsilyl bromide / CH₂Cl₂ / -70 - -50 °C

With dmap; borane-THF; oxalyl dichloride; trimethylsilyl bromide; (1S)-10-camphorsulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 4.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00660-9

Reference yield:

: (3R,4S)-4-Benzyloxy-4-((5R,7S,8R,9S,10S)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-3-methyl-butane-1,2-diol

: 253172-24-6
(2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-2-[(1S,2S)-2-benzyloxy-2-((5R,7R,8R,9S,10S)-8-hydroxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-octahydro-1,5-dioxa-benzocycloocten-3-one

Guidance literature:: Multi-step reaction with 8 steps

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

2.1: 437 mg / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

3.1: 75 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine; 10-camphorsulfonic acid / CH₂Cl₂ / 24 h / 35 °C

4.1: 63 percent / tetrahydrofuran / 60 °C

5.1: BH₃*THF / tetrahydrofuran / 0 - 20 °C

5.2: 75 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

6.1: 57 percent / DMSO; (COCl)2; triethylamine / CH₂Cl₂ / 1.5 h / -70 - -40 °C

7.1: 58 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 12 h / 20 °C

8.1: trimethylsilyl bromide / CH₂Cl₂ / -70 - -50 °C

With dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; trimethylsilyl bromide; (1S)-10-camphorsulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 6.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00660-9