(S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

Base Information

Chemical Name:(S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol
CAS No.:503609-58-3
Molecular Formula:C₄₅H₆₂O₈S₂
Molecular Weight:795.114
Hs Code.:

(S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

Synonyms:(S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

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Chemical Property of (S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

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Technology Process of (S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

There total 9 articles about (S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol 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: 51.0%

: 200186-27-2
(4R,5S,6S)-4-(4-Benzyloxy-butyl)-6-[1,3]dithian-2-ylmethyl-2,2,5-trimethyl-[1,3]dioxane

: 503609-54-9
(2R,3R,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde

: 503609-58-3
(S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: (4R,5S,6S)-4-(4-Benzyloxy-butyl)-6-[1,3]dithian-2-ylmethyl-2,2,5-trimethyl-[1,3]dioxane; With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 - -50 ℃; for 0.666667h;

With cerium(III) chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 2.5h;

(2R,3R,4R,5S)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde; With zinc(II) chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; at -78 ℃; for 4h; Further stages.;
DOI:10.1021/ol034037a

Reference yield:

: 100-39-0
benzyl bromide

: 503609-58-3
(S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: tetrabutylammonium iodide / 36 h / 20 °C

2.1: 10-camphorsulfonic acid / methanol; H₂O / 20 °C

3.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

4.1: 93 percent / TfOH / diethyl ether

5.1: (DHQD)2PYR; K₃Fe(CN)6; aq. K₂CO₃ / K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / 0 °C

6.1: NaOMe

7.1: 95 percent / SO₃*Pyr; DMSO / CH₂Cl₂ / 0 °C

8.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.67 h / -78 - -50 °C

8.2: CeCl₃ / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2.5 h / -78 °C

8.3: 51 percent / ZnCl₂ / tetrahydrofuran; diethyl ether; hexamethylphosphoric acid triamide / 4 h / -78 °C

With dmap; n-butyllithium; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; pyridine-SO₃ complex; trifluorormethanesulfonic acid; (1S)-10-camphorsulfonic acid; sodium methylate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; 5.1: Sharpless asymmetric dihydroxylation / 7.1: Parikh-Doering oxidation;
DOI:10.1021/ol034037a

Reference yield:

: 160797-23-9
(1R,2S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-but-3-en-1-ol

: 503609-58-3
(S)-{2-[(4S,5S,6R)-6-(4-Benzyloxy-butyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: tetrabutylammonium iodide / 36 h / 20 °C

2.1: 10-camphorsulfonic acid / methanol; H₂O / 20 °C

3.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

4.1: 93 percent / TfOH / diethyl ether

5.1: (DHQD)2PYR; K₃Fe(CN)6; aq. K₂CO₃ / K₂OsO₂(OH)4 / 2-methyl-propan-2-ol / 0 °C

6.1: NaOMe

7.1: 95 percent / SO₃*Pyr; DMSO / CH₂Cl₂ / 0 °C

8.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.67 h / -78 - -50 °C

8.2: CeCl₃ / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2.5 h / -78 °C

8.3: 51 percent / ZnCl₂ / tetrahydrofuran; diethyl ether; hexamethylphosphoric acid triamide / 4 h / -78 °C

With dmap; n-butyllithium; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; pyridine-SO₃ complex; trifluorormethanesulfonic acid; (1S)-10-camphorsulfonic acid; sodium methylate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; 5.1: Sharpless asymmetric dihydroxylation / 7.1: Parikh-Doering oxidation;
DOI:10.1021/ol034037a