2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-[(4S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-hexyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-[(4S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-hexyl ester
• CAS No.: 110087-68-8
• Molecular Formula: C₃₂H₅₆O₆Si
• Molecular Weight: 564.879

Synonyms:2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-[(4S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-hexyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-[(4S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-hexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-[(4S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-hexyl ester

There total 17 articles about 2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-[(4S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-hexyl 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: 72.0%

benzyl bromide (100-39-0) + 2,2-Dimethyl-propionic acid (S)-4-[(4S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-6-hydroxy-hexyl ester (110087-67-7) → 2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-[(4S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-hexyl ester (110087-68-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)85204-1

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-2-(2-propenyl)-α-D-allohexopyranoside (126108-10-9) → 2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-[(4S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-hexyl ester (110087-68-8)

Guidance literature:

Multi-step reaction with 16 steps

1: CSA, CH₃OH

3: 1.) phosgene iminium chloride

4: toluene / 100 °C

5: 85 percent / H₂SO₄ / tetrahydrofuran; H₂O / 25 °C

6: 62 percent / PdCl₂/CuCl₂/O₂ / dimethylformamide; H₂O / 25 °C

7: 87 percent / PDC / acetic anhydride; CH₂Cl₂

8: 91 percent / LiAlH₄ / diethyl ether

9: 88 percent / pyridine

10: 60 percent / BF₃*Et₂O

11: 92 percent / imidazole

12: HgCl₂, CaCO₃ / acetonitrile; H₂O

13: 58 percent / tetrahydrofuran

14: 95 percent / PPTS

15: 1.) BH₃*THF, 2.) 3N NaOH, 30percent H₂O₂

16: 72 percent / NaH, n-Bu₄NI / dimethylformamide

With pyridine; 1H-imidazole; methanol; sodium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; borane-THF; sulfuric acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; dihydrogen peroxide; oxygen; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; dichloromethylenedimethyliminium chloride; calcium carbonate; mercury dichloride; copper dichloride; palladium dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic anhydride; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)85204-1

Reference yield:

(1S,2R,3R,4S,5R)-4-(3-Hydroxy-propyl)-2-methyl-6,8-dioxa-bicyclo[3.2.1]octan-3-ol (110087-61-1) → 2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-[(4S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-hexyl ester (110087-68-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / pyridine

2: 60 percent / BF₃*Et₂O

3: 92 percent / imidazole

4: HgCl₂, CaCO₃ / acetonitrile; H₂O

5: 58 percent / tetrahydrofuran

6: 95 percent / PPTS

7: 1.) BH₃*THF, 2.) 3N NaOH, 30percent H₂O₂

8: 72 percent / NaH, n-Bu₄NI / dimethylformamide

With pyridine; 1H-imidazole; sodium hydroxide; borane-THF; boron trifluoride diethyl etherate; dihydrogen peroxide; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; calcium carbonate; mercury dichloride; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(00)85204-1

upstream raw materials:

benzyl bromide

2,2-Dimethyl-propionic acid (S)-4-[(4S,5R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-6-hydroxy-hexyl ester

methyl 4,6-O-benzylidene-2-deoxy-2-(2-propenyl)-α-D-allohexopyranoside

(1S,2R,3R,4S,5R)-4-(3-Hydroxy-propyl)-2-methyl-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

Downstream raw materials:

2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-[(4S,5S,6R)-6-(2-hydroxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-hexyl ester

2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-((4S,5S,6R)-2,2,5-trimethyl-6-vinyl-[1,3]dioxan-4-yl)-hexyl ester

2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-((4S,5R,6S)-6-formyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hexyl ester

2,2-Dimethyl-propionic acid (S)-6-benzyloxy-4-((4S,5R,6S)-6-hydroxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hexyl ester

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