(3S,4R,5S)-4-(3,4-dimethoxybenzyloxy)-5-<2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypyranyl>-3-methylhexane

Base Information

• Chemical Name: (3S,4R,5S)-4-(3,4-dimethoxybenzyloxy)-5-<2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypyranyl>-3-methylhexane
• CAS No.: 102851-97-8
• Molecular Formula: C₂₆H₄₂O₅
• Molecular Weight: 434.616
• Mol file: 102851-97-8.mol

Synonyms:(3S,4R,5S)-4-(3,4-dimethoxybenzyloxy)-5-<2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypyranyl>-3-methylhexane

Chemical Property of (3S,4R,5S)-4-(3,4-dimethoxybenzyloxy)-5-<2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypyranyl>-3-methylhexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5S)-4-(3,4-dimethoxybenzyloxy)-5-<2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypyranyl>-3-methylhexane

There total 3 articles about (3S,4R,5S)-4-(3,4-dimethoxybenzyloxy)-5-<2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypyranyl>-3-methylhexane 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: 95.0%

(3S,4R,5S)-4-hydroxy-5(2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypropanyl)-3-methylhexane (102851-96-7) + 4-chloromethyl-1,2-dimethoxy-benzene (7306-46-9) → (3S,4R,5S)-4-(3,4-dimethoxybenzyloxy)-5-<2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypyranyl>-3-methylhexane (102851-97-8)

Guidance literature:

With potassium dimsylate; Ambient temperature;

DOI:10.1021/ja00275a063

Reference yield:

(2S,3R,5S,6S)-2-isopropyloxy-3,5-dimethyl-6-<1(S)-methyl-2-hydroxyethyl>tetrahydropyran (90093-98-4) → (3S,4R,5S)-4-(3,4-dimethoxybenzyloxy)-5-<2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypyranyl>-3-methylhexane (102851-97-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / Me₂SO, (COCl)2, Et₃N / CH₂Cl₂

2: 94 percent / BF₃-Et₂O / CH₂Cl₂ / -90 °C

3: 95 percent / KCH₂S(O)Me / Ambient temperature

With oxalyl dichloride; boron trifluoride diethyl etherate; potassium dimsylate; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1021/ja00275a063

Reference yield:

(R)-2-((2S,3S,5R,6S)-6-Isopropoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-propionaldehyde (102851-95-6) → (3S,4R,5S)-4-(3,4-dimethoxybenzyloxy)-5-<2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypyranyl>-3-methylhexane (102851-97-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / BF₃-Et₂O / CH₂Cl₂ / -90 °C

2: 95 percent / KCH₂S(O)Me / Ambient temperature

With boron trifluoride diethyl etherate; potassium dimsylate; In dichloromethane;

DOI:10.1021/ja00275a063

upstream raw materials:

(3S,4R,5S)-4-hydroxy-5(2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypropanyl)-3-methylhexane

4-chloromethyl-1,2-dimethoxy-benzene

(2S,3R,5S,6S)-2-isopropyloxy-3,5-dimethyl-6-<1(S)-methyl-2-hydroxyethyl>tetrahydropyran

(R)-2-((2S,3S,5R,6S)-6-Isopropoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-propionaldehyde

Downstream raw materials:

(1R,2R)-2-benzyloxy-1-ethyl-2-formylpropyl (2R,3S,4R,5S,6S,8R)-3-(3,4-dimethoxybenzyloxy)-10-dimethoxyphosphono-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-oxo-decanate

(3R,4S,5R,6S,7S,9R,13R,14R)-13-benzyloxy-4-(3,4-dimethoxybenzyloxy)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,10-dione

[(3R,5S,6S,7R,8R,9S)-8-(3,4-Dimethoxy-benzyloxy)-10,11-dihydroxy-6-(4-methoxy-benzyloxy)-3,5,7,9-tetramethyl-2-oxo-undecyl]-phosphonic acid dimethyl ester

(2R,3S,4R,5S,6S,8R)-3-(3,4-dimethoxybenzyloxy)-10-dimethoxyphosphono-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-oxodecanoic acid