(2S,3R)-4-[(2S,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-trityloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-3-(4-methoxy-benzyloxy)-2-methyl-butan-1-ol

Base Information

• Chemical Name: (2S,3R)-4-[(2S,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-trityloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-3-(4-methoxy-benzyloxy)-2-methyl-butan-1-ol
• CAS No.: 281670-42-6
• Molecular Formula: C₄₉H₆₆O₈Si
• Molecular Weight: 811.144

Synonyms:(2S,3R)-4-[(2S,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-trityloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-3-(4-methoxy-benzyloxy)-2-methyl-butan-1-ol

Chemical Property of (2S,3R)-4-[(2S,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-trityloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-3-(4-methoxy-benzyloxy)-2-methyl-butan-1-ol

Chemical Property:

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Technology Process of (2S,3R)-4-[(2S,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-trityloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-3-(4-methoxy-benzyloxy)-2-methyl-butan-1-ol

There total 19 articles about (2S,3R)-4-[(2S,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-trityloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-3-(4-methoxy-benzyloxy)-2-methyl-butan-1-ol 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: 86.0%

tert-Butyl-{(2R,4S,6R,8S,10S)-10-methoxy-8-[(4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-ylmethyl]-2-trityloxymethyl-1,7-dioxa-spiro[5.5]undec-4-yloxy}-dimethyl-silane (281670-44-8) → (2S,3R)-4-[(2S,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-trityloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-3-(4-methoxy-benzyloxy)-2-methyl-butan-1-ol (281670-42-6)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -40 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)00237-9

Reference yield:

(2S,4S)-pentane-1,2,3,4-tetraol (92691-36-6) → (2S,3R)-4-[(2S,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-trityloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-3-(4-methoxy-benzyloxy)-2-methyl-butan-1-ol (281670-42-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: AcBr / dioxane / 16 h / 20 °C

1.2: 60 percent / K₂CO₃ / methanol / 1 h / 20 °C

2.1: 61 percent / n-BuLi; HMPA / tetrahydrofuran / 0.5 h / -20 °C

3.1: 85 percent / I₂; NaHCO₃ / H₂O; acetone / 0.5 h / 0 °C

4.1: 91 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / 1 h / 0 °C

5.1: 83 percent / PPTS / CH₂Cl₂ / 1 h / 20 °C

6.1: 95 percent / n-BuLi; HMPA / tetrahydrofuran / 1 h / -20 °C

7.1: 95 percent / NaH / tetrahydrofuran / 2 h / 20 °C

8.1: TFA / H₂O / 1 h / 20 °C

8.2: NaBH₄ / methanol / 0.5 h / 20 °C

9.1: CAN / H₂O; acetonitrile / 0.33 h / 0 °C

9.2: ZnCl₂ / tetrahydrofuran; CH₂Cl₂ / 1 h / 20 °C

10.1: ZnCl₂ / CH₂Cl₂ / 0.5 h / 20 °C

11.1: 71 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

12.1: 81 percent / imidazole / dimethylformamide / 17 h / 50 °C

13.1: 86 percent / DIBAL / CH₂Cl₂ / 0.5 h / -40 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; ammonium cerium(IV) nitrate; Acetyl bromide; iodine; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; zinc(II) chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone; acetonitrile; 1.1: Acetyl-bromination / 1.2: Epoxidation / 2.1: Substitution / 3.1: De-dithioacetalization / 4.1: Reduction / 5.1: Acetalization / 6.1: Substitution / 7.1: Etherification / 8.1: Deprotection / 8.2: Reduction / 9.1: De-dithioacetalization; Spiroacetalization / 9.2: p-Methoxybenzylidenation / 10.1: Isomerization / 11.1: Tritylation / 12.1: Silylation / 13.1: Ring cleavage;

DOI:10.1016/S0040-4039(00)00237-9

Reference yield:

D-Arabitol (488-82-4) → (2S,3R)-4-[(2S,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-trityloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-3-(4-methoxy-benzyloxy)-2-methyl-butan-1-ol (281670-42-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 47 percent

2.1: AcBr / dioxane / 16 h / 20 °C

2.2: 60 percent / K₂CO₃ / methanol / 1 h / 20 °C

3.1: 61 percent / n-BuLi; HMPA / tetrahydrofuran / 0.5 h / -20 °C

4.1: 85 percent / I₂; NaHCO₃ / H₂O; acetone / 0.5 h / 0 °C

5.1: 91 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / 1 h / 0 °C

6.1: 83 percent / PPTS / CH₂Cl₂ / 1 h / 20 °C

7.1: 95 percent / n-BuLi; HMPA / tetrahydrofuran / 1 h / -20 °C

8.1: 95 percent / NaH / tetrahydrofuran / 2 h / 20 °C

9.1: TFA / H₂O / 1 h / 20 °C

9.2: NaBH₄ / methanol / 0.5 h / 20 °C

10.1: CAN / H₂O; acetonitrile / 0.33 h / 0 °C

10.2: ZnCl₂ / tetrahydrofuran; CH₂Cl₂ / 1 h / 20 °C

11.1: ZnCl₂ / CH₂Cl₂ / 0.5 h / 20 °C

12.1: 71 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

13.1: 81 percent / imidazole / dimethylformamide / 17 h / 50 °C

14.1: 86 percent / DIBAL / CH₂Cl₂ / 0.5 h / -40 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; ammonium cerium(IV) nitrate; Acetyl bromide; iodine; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; zinc(II) chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone; acetonitrile; 2.1: Acetyl-bromination / 2.2: Epoxidation / 3.1: Substitution / 4.1: De-dithioacetalization / 5.1: Reduction / 6.1: Acetalization / 7.1: Substitution / 8.1: Etherification / 9.1: Deprotection / 9.2: Reduction / 10.1: De-dithioacetalization; Spiroacetalization / 10.2: p-Methoxybenzylidenation / 11.1: Isomerization / 12.1: Tritylation / 13.1: Silylation / 14.1: Ring cleavage;

DOI:10.1016/S0040-4039(00)00237-9

upstream raw materials:

tert-Butyl-{(2R,4S,6R,8S,10S)-10-methoxy-8-[(4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-ylmethyl]-2-trityloxymethyl-1,7-dioxa-spiro[5.5]undec-4-yloxy}-dimethyl-silane

3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

(2S,4S)-pentane-1,2,3,4-tetraol

D-Arabitol

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