(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 (2R,3S,5S,7R,8S)-7-benzyloxy-8-benzyloxymethyl-2-((Z)-but-2-enyl)-5-methyl-oxocan-3-yl ester

Base Information

• Chemical Name: (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 (2R,3S,5S,7R,8S)-7-benzyloxy-8-benzyloxymethyl-2-((Z)-but-2-enyl)-5-methyl-oxocan-3-yl ester
• CAS No.: 253172-13-3
• Molecular Formula: C₅₀H₆₈O₁₀
• Molecular Weight: 829.084

Synonyms:(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 (2R,3S,5S,7R,8S)-7-benzyloxy-8-benzyloxymethyl-2-((Z)-but-2-enyl)-5-methyl-oxocan-3-yl ester

Chemical Property of (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 (2R,3S,5S,7R,8S)-7-benzyloxy-8-benzyloxymethyl-2-((Z)-but-2-enyl)-5-methyl-oxocan-3-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of (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 (2R,3S,5S,7R,8S)-7-benzyloxy-8-benzyloxymethyl-2-((Z)-but-2-enyl)-5-methyl-oxocan-3-yl ester

There total 16 articles about (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 (2R,3S,5S,7R,8S)-7-benzyloxy-8-benzyloxymethyl-2-((Z)-but-2-enyl)-5-methyl-oxocan-3-yl ester 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: 74.0%

(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 (261776-53-8) + (2R,3S,5R,7R,8S)-7-Benzyloxy-8-benzyloxymethyl-2-((Z)-but-2-enyl)-5-methyl-oxocan-3-ol (253172-16-6) → (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 (2R,3S,5S,7R,8S)-7-benzyloxy-8-benzyloxymethyl-2-((Z)-but-2-enyl)-5-methyl-oxocan-3-yl ester (253172-13-3)

Guidance literature:

With dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 35 ℃;

DOI:10.1039/a906834a

Reference yield:

(2R,3S,4S,4aR,10aS)-2-Allyl-6,6,8,8-tetraisopropyl-2-methoxy-3,4-dimethyl-hexahydro-1,5,7,9-tetraoxa-6,8-disila-benzocyclooctene → (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 (2R,3S,5S,7R,8S)-7-benzyloxy-8-benzyloxymethyl-2-((Z)-but-2-enyl)-5-methyl-oxocan-3-yl ester (253172-13-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: BBN / tetrahydrofuran

1.2: 88 percent / NaOH; H₂O₂ / tetrahydrofuran

2.1: 92 percent / CSA / CH₂Cl₂

3.1: TBAF / tetrahydrofuran

4.1: Et₃N / CH₂Cl₂ / 0 - 20 °C

5.1: iPr₂NEt / CH₂Cl₂ / 0 - 35 °C

6.1: LiAlH₄ / diethyl ether / 0 - 20 °C

7.1: Dess-Martin periodinane / CH₂Cl₂

8.1: molecular sieves 4 Angstroem / toluene / -78 - -60 °C

8.2: NaBH₄ / toluene / -60 - 0 °C

9.1: 89 percent / NaH / tetrahydrofuran; dimethylformamide

10.1: OsO₄; NMO; H₂O / 2-methyl-propan-2-ol

11.1: NaIO₄ / pH 7

12.1: NaClO₂; NaH₂PO₄; 2-methylbut-2-ene / 2-methyl-propan-2-ol; H₂O

13.1: 74 percent / DCC; DMAP; CSA / CH₂Cl₂ / 35 °C

With dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2-methyl-but-2-ene; 4 A molecular sieve; BBN; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; sodium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Addition / 1.2: Oxidation / 2.1: Cyclization / 3.1: Substitution / 4.1: Acylation / 5.1: Etherification / 6.1: Reduction / 7.1: Oxidation / 8.1: Substitution / 8.2: Reduction / 9.1: Etherification / 10.1: Oxidation / 11.1: Oxidation / 12.1: Oxidation / 13.1: Esterification;

DOI:10.1039/a906834a

Reference yield:

((5R,7S,8R,9S,10S)-8-Methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-methanol (253172-18-8) → (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 (2R,3S,5S,7R,8S)-7-benzyloxy-8-benzyloxymethyl-2-((Z)-but-2-enyl)-5-methyl-oxocan-3-yl ester (253172-13-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Dess-Martin periodinane / CH₂Cl₂

2.1: molecular sieves 4 Angstroem / toluene / -78 - -60 °C

2.2: NaBH₄ / toluene / -60 - 0 °C

3.1: 89 percent / NaH / tetrahydrofuran; dimethylformamide

4.1: OsO₄; NMO; H₂O / 2-methyl-propan-2-ol

5.1: NaIO₄ / pH 7

6.1: NaClO₂; NaH₂PO₄; 2-methylbut-2-ene / 2-methyl-propan-2-ol; H₂O

7.1: 74 percent / DCC; DMAP; CSA / CH₂Cl₂ / 35 °C

With dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; 2-methyl-but-2-ene; 4 A molecular sieve; camphor-10-sulfonic acid; water; sodium hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Oxidation / 2.1: Substitution / 2.2: Reduction / 3.1: Etherification / 4.1: Oxidation / 5.1: Oxidation / 6.1: Oxidation / 7.1: Esterification;

DOI:10.1039/a906834a

upstream raw materials:

(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

(2R,3S,5R,7R,8S)-7-Benzyloxy-8-benzyloxymethyl-2-((Z)-but-2-enyl)-5-methyl-oxocan-3-ol

(5R,7R,8R,9S,10S)-8-Methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane-7-carbaldehyde

((5R,7S,8R,9S,10S)-8-Methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-methanol

Downstream raw materials:

7-benzyloxy-2-[2-benzyloxy-2-(8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-4,4a,6,7,8,9,10,10a-octahydro-1,5-dioxa-benzocyclooctene

(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

(2S,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

(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-decahydro-1,5-dioxa-benzocycloocten-3-ol

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