(2S,3S)-3-{2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-2-methyl-butyraldehyde

Base Information

• Chemical Name: (2S,3S)-3-{2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-2-methyl-butyraldehyde
• CAS No.: 552890-64-9
• Molecular Formula: C₂₇H₃₆O₄S₂
• Molecular Weight: 488.712

Synonyms:(2S,3S)-3-{2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-2-methyl-butyraldehyde

Chemical Property of (2S,3S)-3-{2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-2-methyl-butyraldehyde

Chemical Property:

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Technology Process of (2S,3S)-3-{2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-2-methyl-butyraldehyde

There total 1 articles about (2S,3S)-3-{2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-2-methyl-butyraldehyde 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: 99.0%

(2R,3S,4S,5S)-1-Benzyloxy-5-{2-[(S)-2-benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-4-methyl-hexane-2,3-diol (552890-45-6) → (2S,3S)-3-{2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-2-methyl-butyraldehyde (552890-64-9)

Guidance literature:

With lead(IV) acetate; In dichloromethane;

DOI:10.1055/s-2003-37533

Reference yield: 89.0%

trimethylsilylacetylene (1066-54-2) + (2S,3S)-3-{2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-2-methyl-butyraldehyde (552890-64-9) + methyl iodide (74-88-4) → ((4S,5S)-5-{2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-3-methoxy-4-methyl-hex-1-ynyl)-trimethyl-silane (617673-31-1)

Guidance literature:

trimethylsilylacetylene; With tert.-butyl lithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.25h;

(2S,3S)-3-{2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-2-methyl-butyraldehyde; In tetrahydrofuran; hexane; at 0 ℃; for 0.333333h;

methyl iodide; In tetrahydrofuran; hexane; at 20 ℃; for 2.5h;

DOI:10.1016/S0040-4020(03)00873-1

Reference yield:

(2S,3S)-3-{2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-2-methyl-butyraldehyde (552890-64-9) → C35H46O8 (552890-55-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: t-BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C

1.2: tetrahydrofuran; hexane / 0.33 h / 0 °C

1.3: 89 percent / tetrahydrofuran; hexane / 2.5 h / 20 °C

2.1: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C

3.1: N-chlorosuccinimide; AgNO₃; 2,4,6-collidine / acetonitrile; H₂O / 0.08 h / -10 °C

3.2: 51 percent / NaBH₄ / methanol / 0.5 h / 0 °C

4.1: 98 percent / pyridine / acetonitrile / 5 h / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

5.2: tetrahydrofuran; hexane / 2.5 h

5.3: 80 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

6.1: 100 percent / PPTS / CH₂Cl₂ / 1.5 h / 20 °C

7.1: 88 percent / TBAF / tetrahydrofuran / 144 h / 50 °C

8.1: 100 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 20 °C

9.1: 91 percent / camphorsulfonic acid / methanol / 0.08 h / 20 °C

10.1: Co(CO)8 / CH₂Cl₂ / 2 h / 20 °C

10.2: BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / 0 °C

10.3: 81.0 mg / bis*trimethylsilyl)acetylene; n-Bu₃SnH / toluene / 0.5 h / 60 °C

11.1: 93 percent / K₂CO₃ / tetrahydrofuran; methanol / 20 °C

12.1: 94 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C / 3 Torr

13.1: 98 percent / IBX / dimethylsulfoxide / 4 h / 20 °C

14.1: 85 percent / PdCl₂; CuCl; O₂ / dimethylformamide; H₂O / 20 °C

15.1: AD-mix-α; methylsulfonamide / 2-methyl-propan-2-ol; H2O / 0 °C

15.2: 72 percent / HF*pyridine / acetonitrile / 0.5 h / 20 °C

16.1: 82 percent / Na₂HPO₄; Hg-Na / methanol / 4.5 h

With pyridine; 2,4,6-trimethyl-pyridine; dmap; disodium hydrogenphosphate; AD-mix-α; N-chloro-succinimide; n-butyllithium; Co(CO)8; methanesulfonamide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; oxygen; sodium; pyridinium p-toluenesulfonate; potassium carbonate; silver nitrate; triethylamine; mercury; copper(l) chloride; palladium dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4020(03)00873-1

upstream raw materials:

(2R,3S,4S,5S)-1-Benzyloxy-5-{2-[(S)-2-benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-4-methyl-hexane-2,3-diol

Downstream raw materials:

((4S,5S)-5-{2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-[1,3]dithian-2-yl}-3-methoxy-4-methyl-hex-1-ynyl)-trimethyl-silane

(2S,5S,6S)-2-Benzyloxy-7-methoxy-1-(4-methoxy-benzyloxy)-5,6-dimethyl-non-8-yn-4-ol

2-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-2-((1S,2S)-3-methoxy-1,2-dimethyl-pent-4-ynyl)-[1,3]dithiane

{(2S,3S)-1-[(S)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-propyl]-4-methoxy-2,3-dimethyl-hex-5-ynyloxy}-tert-butyl-dimethyl-silane

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