(1S,4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenol

Base Information

• Chemical Name: (1S,4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenol
• CAS No.: 338460-85-8
• Molecular Formula: C₁₃H₂₆O₃Si
• Molecular Weight: 258.433
• Mol file: 338460-85-8.mol

Synonyms:(1S,4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenol

Chemical Property of (1S,4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenol

There total 6 articles about (1S,4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenol 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%

(4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenone (338460-84-7) → (1S,4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenol (338460-85-8)

Guidance literature:

With sodium tris(acetoxy)borohydride; In acetic acid; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)00032-1

Reference yield:

(1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-1,2-dicarboxylic acid dimethyl ester (203627-51-4) → (1S,4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenol (338460-85-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / imidazole / dimethylformamide / 10 h / 60 °C

2: 89 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 °C

3: 80 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.33 h

4: 95 percent / NaBH(OAc)3 / acetic acid / 0.5 h / 20 °C

With 1H-imidazole; sodium periodate; lithium aluminium tetrahydride; sodium tris(acetoxy)borohydride; In tetrahydrofuran; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)00032-1

Reference yield:

(1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,6-bis-hydroxymethyl-cyclohex-2-enol (338460-92-7) → (1S,4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenol (338460-85-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.33 h

2: 95 percent / NaBH(OAc)3 / acetic acid / 0.5 h / 20 °C

With sodium periodate; sodium tris(acetoxy)borohydride; In tetrahydrofuran; water; acetic acid;

DOI:10.1016/S0040-4020(01)00032-1

upstream raw materials:

(4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenone

tert-butyldimethylsilyl chloride

(1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-1,2-dicarboxylic acid dimethyl ester

(1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,6-bis-hydroxymethyl-cyclohex-2-enol

Downstream raw materials:

5a-carba-α-D-mannopyranose

(1S,2R,3S,4R,5R)-5-(acetoxymethyl)cyclohexane-1,2,3,4-tetrayl tetraacetate

5a-carba-α-D-mannopyranose-6-phosphate

tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-mannopyranoside