(3S,4S)-4-Benzyloxymethyl-3-(tetrahydro-pyran-2-yloxy)-2-[(S)-4-(tetrahydro-pyran-2-yloxy)-pent-1-ynyl]-tetrahydro-furan-2-ol

Base Information

• Chemical Name: (3S,4S)-4-Benzyloxymethyl-3-(tetrahydro-pyran-2-yloxy)-2-[(S)-4-(tetrahydro-pyran-2-yloxy)-pent-1-ynyl]-tetrahydro-furan-2-ol
• CAS No.: 892397-48-7
• Molecular Formula: C₂₇H₃₈O₇
• Molecular Weight: 474.595
• Mol file: 892397-48-7.mol

Synonyms:(3S,4S)-4-Benzyloxymethyl-3-(tetrahydro-pyran-2-yloxy)-2-[(S)-4-(tetrahydro-pyran-2-yloxy)-pent-1-ynyl]-tetrahydro-furan-2-ol

Chemical Property of (3S,4S)-4-Benzyloxymethyl-3-(tetrahydro-pyran-2-yloxy)-2-[(S)-4-(tetrahydro-pyran-2-yloxy)-pent-1-ynyl]-tetrahydro-furan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-Benzyloxymethyl-3-(tetrahydro-pyran-2-yloxy)-2-[(S)-4-(tetrahydro-pyran-2-yloxy)-pent-1-ynyl]-tetrahydro-furan-2-ol

There total 1 articles about (3S,4S)-4-Benzyloxymethyl-3-(tetrahydro-pyran-2-yloxy)-2-[(S)-4-(tetrahydro-pyran-2-yloxy)-pent-1-ynyl]-tetrahydro-furan-2-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:

(S)-2-<(tetrahydro-2H-pyran-2-yl)oxy>-4-pentyne (81969-74-6) + (2S,3S)-3-benzyloxymethyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]-4-butanolide (383368-61-4) → (3S,4S)-4-Benzyloxymethyl-3-(tetrahydro-pyran-2-yloxy)-2-[(S)-4-(tetrahydro-pyran-2-yloxy)-pent-1-ynyl]-tetrahydro-furan-2-ol (892397-48-7)

Guidance literature:

(S)-2-<(tetrahydro-2H-pyran-2-yl)oxy>-4-pentyne; With methyllithium; In diethyl ether; pentane; at 0 ℃; for 0.0833333h;

(2S,3S)-3-benzyloxymethyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]-4-butanolide; In diethyl ether; pentane; at 0 - 20 ℃; for 3.33333h;

DOI:10.1021/jo060149e

Reference yield:

(3S,4S)-4-Benzyloxymethyl-3-(tetrahydro-pyran-2-yloxy)-2-[(S)-4-(tetrahydro-pyran-2-yloxy)-pent-1-ynyl]-tetrahydro-furan-2-ol (892397-48-7) → (3S,4S,5R,7S)-4-Benzyloxy-3-benzyloxymethyl-7-methyl-1,6-dioxa-spiro[4.5]decane

Guidance literature:

Multi-step reaction with 5 steps

1.1: 88 mg / hydrochloric acid / 1 h / 20 °C

2.1: hydrogen / rhodium on activated Al₂O₃ / methanol / 4.5 h / 20 °C / 760 Torr

2.2: 10 percent / hydrochloric acid / 15 h / 20 °C

3.1: 82 percent / hydrogen / palladium on carbon / methanol / 4 h / 20 °C / 760 Torr

4.1: 14 percent / sodium hydride / dimethylformamide; various solvent(s) / 20 h / 20 °C

5.1: hydrochloric acid / tetradeuteriomethanol / 48 h / 20 °C

With hydrogenchloride; hydrogen; sodium hydride; palladium on activated charcoal; rhodium on alumina; In methanol; d⁽⁴⁾-methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo060149e

Reference yield:

(3S,4S)-4-Benzyloxymethyl-3-(tetrahydro-pyran-2-yloxy)-2-[(S)-4-(tetrahydro-pyran-2-yloxy)-pent-1-ynyl]-tetrahydro-furan-2-ol (892397-48-7) → (3R,4S,5S,7S)-4-(4-bromophenylcarbonyloxy)-7-methyl-1,6-dioxaspiro[4.5]dec-3-yl-methyl 4-bromobenzoate

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88 mg / hydrochloric acid / 1 h / 20 °C

2.1: hydrogen / rhodium on activated Al₂O₃ / methanol / 4.5 h / 20 °C / 760 Torr

2.2: 10 percent / hydrochloric acid / 15 h / 20 °C

3.1: 82 percent / hydrogen / palladium on carbon / methanol / 4 h / 20 °C / 760 Torr

4.1: 16 percent / ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

With hydrogenchloride; dmap; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; rhodium on alumina; In methanol; dichloromethane;

DOI:10.1021/jo060149e

upstream raw materials:

(S)-2-<(tetrahydro-2H-pyran-2-yl)oxy>-4-pentyne

(2S,3S)-3-benzyloxymethyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]-4-butanolide

Downstream raw materials:

(2R,3S,4S)-4-benzyloxymethyl-2-[(S)-4-hydroxypent-1-ynyl]-2-methoxytetrahydrofuran-3-ol

(3S,4S,5S,7S)-3-benzyloxymethyl-7-methyl-1,6-dioxaspiro[4.5]-decan-4-ol

(3S,4S,5S,7S)-4-benzyloxy-3-benzyloxymethyl-7-methyl-1,6-dioxaspiro[4.5]decane